Optically pure 1-amido-2-indanols

Details Optically pure 1-amido-2-indanols Optically pure 1-amido-2-indanols

1994-07-21

1997-02-04

Burn, Brian M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564222, C07C23306

Patent

active

055999859

ABSTRACT:
A two-step process for the conversion of a trans-1-amino-2-hydroxycycloalkane stereoselectively to a cis-1-amino-2-hydroxycycloalkane is disclosed. The novel step, a one-step hydrolysis with formal inversion, can be used to convert an amide of a trans-1-amino-2-hydroxycycloalkane to a cis-1-amino-2-hydroxycycloalkane. Methods for obtaining the trans-1-amino-2-hydroxycycloalkanes and their amides from alkenes are also disclosed. Novel, optically active 1-amido-2-indanols and 1-amino-2-alkanols are also disclosed.

REFERENCES:
patent: 5043341 (1991-08-01), Cohen et al.
Tucker et al. "A Series of Potent HIV-1 Protease Inhibitors Containing a . . . " J. Med. Chem. 35, 2525-33 (1992).
Young et al. "HIV-1 Protease Inhibitors Based on Hydroxyethylene . . . " J. Med. Chem. 35, 1702-1709 (1992).
Thompson et al. "Synthesis and Antiviral Activity of a Series of HIV-1 . . . " J. Med. Chem. 35, 1685-1701 (1992).
Armstrong et al. "Stereocontrolled Addition of Chiral, Non-Racemic Amide . . . " Tetrahedron Letters 33, 6599-6602 (1992).
Lutz et al. "Further Studies on the Stability of .beta.-Hydroxyethylamines . . . " J. Am. Chem. Soc. 73, 1639-1641 (1951).
Jacobsen et al. "Highly Enantioselective Epoxidation Catalysts Derived from 1,2-Diaminocyclohexane" J. Am. Chem. Soc. 113, 7063-64 (1991).
Askin et al. "Highly Diastereoselective Alkylations of Chiral Amide" J. Org. Chem. 57, 2771-2773 (1992).
Lyle et al. "Benzocycloalkyl Amines as Novel C-Termini for . . . " J. Med. Chem. 34, 1228-1230 (1991).
McCasland et al. "Stereochemistry of Aminocyclanols. Synthesis of . . . " J. Amn. Chem. Soc. 72, 2190-2195 (1950).
Bannard et al. "Reaction of trans-2-Acylaminocyclanols with Thionyl Chloride" Can. J. Chem. 49, 2064-2072 (1970).
McCarthy et al. "Stereospecific Syntheses of the Four Diasteromeric" J. Org. Chem. 50, 3095-3103 (1985).
Ghosh et al. "Stereoselective Reduction of .alpha.-Hydroxy Oxime Ethers . . . " Tetrahedron Letters 32, 711-714 (1991).
Hassner et al. "Addition of Iodine Isocyanate to Olefins . . . " J. org. Chem. 32, 540-549 (1967).
Johnson et al. "Ring Closure of the 2-Benzoylaminocyclohexanols . . . " J. Am. Chem. Soc. 72, 2187-2190 (1950).
Winstein et al. "The Role of Neighboring Groups in Replacement Reactions . . . " J. Am. Chem. Soc. 72, 4669-4677 (1950).
Pracejus et al. "O,N-Bis(diphenylphosphino) derivatives of chiral trans-and cis-2-aminocyclohexanols: synthesis . . . " J. Prakt. Chem. 329, 235-45 (1987).
Kotora et al. "Addition of tetrachloromethane to styrene catalyzed by copper-chiral amine complexes" Coll. Czech. Chem. Commun. 56, 2622-8 (1992).
Didier et al. "Chemo-enzymatic Synthesis of 1,2-and 1,3-amino alcohols and their use in the . . . " Tetrahedron 47, 4941-58 (1991).
Drefahl et al. "Aminoalkohole, I: cis- und trans-DL-1-Amino-2-hydroxy-tetralin und . . . " Chemische Beriuchte 91, 266-70 (1958).
Braun et al. "Alkamine und Ather-basen der Tetralin- und Hydrinden-Reihe" Chemische Berichte 73, 3052-59 (1930).
CA52:16418 (d) (1958).
CA54:13079 (e) (1960).

Affiliated with

Also associated with

Rating

Optically pure 1-amido-2-indanols does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Optically pure 1-amido-2-indanols, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Optically pure 1-amido-2-indanols will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-680283