Process for diastereoselective reduction of 3-amino-1-benzoxepin

Details Process for diastereoselective reduction of 3-amino-1-benzoxepin Process for diastereoselective reduction of 3-amino-1-benzoxepin

1987-10-20

1989-05-16

Raymond, Richard L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D31308

Patent

active

048311677

ABSTRACT:
A process for producing cis-2,3,4,5-tetrahydro-3-amino-1-benzoxepin-5-ols in which 3-amino-1-benzoxepin-5(2H)-ones are diastereoselectively reduced in a single stage by catalytic hydrogenation in the presence of a platinum oxide catalyst and an equivalent amount of an acid in a polar protic solvent, or by reaction with a borane/amine complex in an aprotic solvent, optionally in the presence of an added lower aliphatic carboxylic acid.

REFERENCES:
patent: 4279904 (1981-07-01), Ohlendorf et al.
patent: 4279905 (1981-07-01), Ohlendorf et al.
S. Mitsui et al, Tetrahedron, vol. 29 (1973), pp. 1531-1539.
M. J. F. Burman et al, Tetrahedron Letters, No. 18 (1976), pp. 1535-1538.
David C. Horwell et al, Chemical Abstracts 90:168189a (1979).
F. Van Rantwijk et al, Chemical Abstracts 95:61284d (1981).
Baker, et al, "The Reduction of Amide Vinylogs", J. Am. Chem. Soc., 68:2009-11 (1946).
Kochetkov, "Beta-Aminovinyl Ketones II", Chem. Abstracts, 49:6090i (1955).
Bowden, et al, "Researches on Acetylenic Compounds. Part II", J. Chem. Soc., (1946), pp. 45-52.
Horwell, et al, "Stereoselectivity in the Catalytic Hydrogenation of an Enamine.", Synthetic Communications, 9(3):223-31 (1979).
Martin, et al, "Ketones VIII. Some Reactions of 1-(Dimethylamino)-4-methyl-1-penten-3-one", J. Org. Chem., 31:943-6 (1966).
Greenhill, et al, "Reduction of Enaminones in the Preparation of 3-Aminocyclohexanols", J. C. S. Perkin I., pp. 588-591 (1975).
Greenhill, "Enaminones", Chem. Soc. Reviews, 6:277-95 (1977).
Phillips et al., Jour. Amer. Chem. Soc., vol. 78, pp. 140-145 (1956).
Albertson, Jour. Amer. Chem. Soc., vol. 74, pp. 249-251 (1952).

Affiliated with

Also associated with

Rating

Process for diastereoselective reduction of 3-amino-1-benzoxepin 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 diastereoselective reduction of 3-amino-1-benzoxepin, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for diastereoselective reduction of 3-amino-1-benzoxepin will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2323987