Process for the preparation of (R)-2-alkyl-3-phenyl-1-propanols

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C568S610000, C568S630000, C568S648000, C568S649000, C568S651000, C568S656000, C568S658000, C568S715000, C568S812000, C560S055000, C560S060000, C560S064000

Reexamination Certificate

active

06881868

ABSTRACT:
Compounds of formula (I), wherein R1and R2are, independently of one another, H,C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxyl, C1-C6alkoxy-C1-C6alkyl, or C1-C6alkoxy-C1-C6alkyloxy, and R3is C1-C6alkyl, are obtainable in high yiedls by stereoselective addition of R3-substituted propionic acid esters to R1- and R2-substituted benzaldehydes of formula R—CHO to form corresponding 3-R-3-hydroxy-2-R3-propionic acid esters, conversion of the OH group to a leaving group, subsequent regioselective elimination to form 3-R-2-R3-propenic acid esters, and reduction to corresponding 3-R-2-R3-allyl alcohols and their enantioselective hydrogenation, wherein R is (a).

REFERENCES:
patent: 4767768 (1988-08-01), Okamoto et al.
patent: 5723642 (1998-03-01), Sturmer et al.
patent: 195 16 968 (1996-11-01), None
patent: 406025093 (1994-02-01), None
Bhatia et al., Synthesis of 1-(4′-Methoxy-1′-phenyl)allyl Citronellyl Ether and Related Substances, Journal of Indian Chemical Society, vol. 64(7), Jul. 1987, pp. 411-413.*
Hulskamper et al., Mechanism of the Substitution at the Cyclopropane Ring, Chemische Berichte, May 1981, vol. 114(2),pp. 746-756.*
Knsomasekharan et al.,Conformational Analysis of 1,1,2-Trisubstituted Ethanes by PMR Part 1-3-Aryl-2-methylpropanols, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, vol. 27B(1), Jan. 1988, pp. 29-37.*
Journal o f the Indian Chemical Society, 1987, 64(7), pp. 411-413.*
Chemische Berichte, 1981, 114(2), pp. 746-756.*
Ger. Offen., Nov. 1996, 19516968.*
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, 27B(1), pp. 29-37.*
R. Schmid, et al.: “Axially dissymmetric diphosphines in the biphenyl series: synthesis of (6,6′-dimethoxybiphenyl-2,2′-diyl) bis (diphenylphosphine) (‘MeO-BIPHEP’) and analogs via an ortho-lithiation/iodination Ullmlann-reaction approach”, HELVETICA CHIMICA ACTA, vol. 74, No. 2, Mar. 13, 1991, pp. 370-389, XP002097708, Verlag Helvetica Chimica Acta, Basel, CH.
Y. Wei, et al.: “Aldol addition reaction of a lithium ester enolate in the solid state”, Tetrahedron Letters, vol. 32, No. 12, Mar. 18, 1991, pp. 1535-1538, XP002175158, Elsevier Science Publishers, Amsterdam, NL.
M. Taniguchi, et al.: “Stereoselective reduction of 2-methyl-3-oxo esters (or amides) with sodium borohydride catalyzed by managanese (II) chloride or tetrabutylammonium borohydride. A practical preparation of erythro—and threo-3-hydroxy-2-methyl esters (or amides)”, TETRAHEDRON, vol. 49, No. 48, Nov. 26, 1993, pp. 11169-11182, XP002175159, Elsevier Science Publishers, Amsterdam, NL.
K. Von Auwers, et al.: “Über Cumarunone und Hydrindone” Berichte der Deutschen Chemischen Gesellschaft, vol. 52, 1919, pp. 92-113, XP002175160, Verlag Chemie, Weinheim, DE.
G. Bartoli, et al.: “An efficient procedure for the diastereoselective dehydration of beta-hydroxy carbonyl compounds by CeC13.7H20/Nal system”, ORGANIC LETTERS, vol. 2, No. 13, Jun. 1, 2000, pp. 1791-1793, XP002175161, American Chemical Society, Washington, DC.
G.W. Daub, et al.: “Acyclic stereoselection in the ortho ester Claisen rearrangement”, JOURNAL of ORGANIC CHEMISTRY, vol. 62, No. 7, Apr. 4, 1997, pp. 1976-1985, XP002175162 American Chemical Society, Washington, DC, US.
H. Brunner, et al.: “Hydrierung prochiarler Olefine mit Rhodium-Komplexen von optisch aktiven Amidinen”, MONATSHEFTE FÜR CHEMIE, vol. 111, No. 1, 1980, pp. 275-287, XP002175163 Springer Verlag, Vienna AT.
Liang Li, et al.: “Synthesis of 2-methyl-1,4-naphthquinone-4-C14”, Journal of the American Chemical Society, vol. 74, No. 16, Aug. 20, 1952, pp. 4089-4090, XP002175164 American Chemical Society, Washington, DC., US.
M. Brunner, et al.: “The first stereoselective palladium-catalysed cyclocarbonylation of beta, gamma-substituted allylic alcohols”, Journal of Organic Chemistry, vol. 62, No. 22, Oct. 31, 1997, pp. 7565-7568, XP002175165, American Chemical Society, Washington, DC, US.
M.D. Turnbull: “Productivity in synthesis: a mixture protocol to raise compound output is demonstrated for asymmetric cyclopropanation of allyl alcohols”, Journal of the Chemical Society, Perkin Transactions 1, No. 8, Apr. 21, 1997, pp. 1241-1248, XP002175166, Royal Society of Chemistry, Letchworth, GB.
P. Gramatica, et al.: “Reduction of cinnamyl alcohols and cinnamaldehydes bySaccharomyces cerevisiae”, Bioorganic Chemistry, vol. 10, No. 1, 1981, pp. 22-28, XP00105943, Academic Press, New York, NY, US.
J.K. Crandall, et al.: “Cis reduction of acetylanes by organocopper reagents ”, Journal of Organic Chemistry, vol. 41, No. 26, Dec. 24, 1976, pp. 4089-4092, XP002175168, American Chemical Society, Washington, DC, US.
J.G. Duboudin et al.: “Réactifs de Grignard vinyliques gamma fonctionnels. I. Réactivité des organomagnésiens vis-à-vis d'alcools alpha acétyléniques en présnece d'halogénures cuivreux”, Journal of Organometallic Chemistry, vol. 168, No. 1, Mar. 13, 1979, pp. 1-11, XP002028213, Elsevier Sequoia, Lausanne, CH.
D. Basavaiah, et al.: “Applications of Baylis-Hillman coupling products: a remarkable reversal of stereochemistry from esters to nitriles: a simple synthesis of (2E)-2-methylalk2-en-1-ols and (2Z)-2-methylalk-2-enenitriles”, Journal of the Chemical Society, Chemical Communications., No. 13, Jul. 1, 1992, pp. 955-957, XP002175169, Royal Society of Chemistry, Letchworth, GB.
P.H. Boyle, et al., : “Reaction of ally and benzyl alcohols, and their toluene-p-sulphonates, with furan”, Journal of the Chemical Society, Perkin Transactions 1, No. 13, 1972, pp. 1617-1622, XP002175170, Royal Society of Chemistry, Letchworth, GB.
A. Kamimura, et al.: “Stereoselective thio-Micheal/aldol tandem reaction to alpha, beta-unsaturated esters”, Journal of Organic Chemistry, vol. 64, No. 17, Aug. 4, 1999, pp. 6353-6360, XP002175171, American Chemical Society, Washington, DC, US.
R. Inoue, et al.: “Reaction of tert-butyl dibromoacetate or N, N-diethyldibromoacetamide with trailkylmanganate providing an alkylated manganese enolate”, Journal of Organic Chemistry, vol. 63, No. 4., Jan. 27, 1998, pp. 910-911, XP002175172, American Chemical Society, Washington, DC, US.
B.C. Ranu, et al.: “Surface-mediated solid phase reaction. Part 9. A convenient procedure for aldol reaction of ketene silyl acetals with aldehydes on the solid surface of alumina”, Synthetic Communications, vol. 27, No. 17, 1997, pp. 3065-3077, XP001015930, Marcel Dekker, Basel, CH.
P.M. Bodnar, et al.: “Stereo—and regioselectivity of reactions of siliranes with aldehydes and related substrates”, Journal of Organic Chemistry, vol. 62, No. 14, Jul. 11, 1997, pp. 4737-4745, XP002175174, American Chemical Society, Washington, DC, US.
J. Ezquerra, et al.: “(S)-Ethyl 4,4-dimethyl pyroglutamate as a new ‘ quat’ chiral auxiliary in aldol condensations” Tetrahedron: Asymmetry, vol. 8, No. 5, Mar. 13, 1997, pp. 669-671, XP004055877, Elsevier Science Publishers, Amsterdam, NL.
K. Takai et al.: “Sequential generation and utilisation of radical and anionic species with a novel manganese-lead reducing agent. Three-component coupling reactions of alkyl iodides, electron-deficient olefins, and carbonyl compounds”, Journal of Organic Chemistry, vol. 61, No. 23, Nov. 15, 1996, pp. 7990-7991, XP002175175, American Chemical Society, Washington, DC, US.
Y Han, et al.: “Metallic gallium-promoted Reformatsky-type reaction”, Chinese Chemical Letters, vol. 7, No. 8, 1996, pp. 713-716, XP001015981, Chinese Chemical Bureau, Beijing, CN.
J.J. Juarez -Brambila et al.: “Use of mesityllithium in the alpha-alkylation reaction of B-alkyl-9-borabicyclo'3.3.1Inonanes”, Journal of the Indian Institute of Sciences, vol. 74, No. 1

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Process for the preparation of (R)-2-alkyl-3-phenyl-1-propanols does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the preparation of (R)-2-alkyl-3-phenyl-1-propanols, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of (R)-2-alkyl-3-phenyl-1-propanols will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3421174

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.