Direct isolution of optically pure (3S)-1,2,3,4-tetrahydroisoqui

Details Direct isolution of optically pure (3S)-1,2,3,4-tetrahydroisoqui Direct isolution of optically pure (3S)-1,2,3,4-tetrahydroisoqui

1995-03-14

1997-03-11

Davis, Zinna Northington

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D21702

Patent

active

056103077

ABSTRACT:
A substantially pure L-isomer of (3S) 1,2,3,4-tetrahydro-isoquinoline is produced from an optically enriched mixture by cyclizing D- or L-phenylalanine using a solution of formaldehyde and hydrochloric acid, adjusting the pH of the mixture to yield the neutral free acid form and treating the mixture with dilute acetic acid of from about 5.0 wt/wt % to about 25 wt/wt %. The mixture is then refluxed at 80.degree. C. to 95.degree. C. and cooled to about 10.degree. C. to yield amorphous powdery solid material.

REFERENCES:
Hayashi et al, Chemical & Pharmaceutical Bulletin, vol. 31, No. 1, Jan. 1983, pp. 312-314.
O'Reilly et al, Synthesis, No. 7, Jul. 1990, pp. 550-556.
Shiraiwa et al, Bull. Chem. Soc. Jpn. vol. 64, No. 12, 1991, pp. 3729-3731.

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