Process for stereoselectively reducing indole derivatives

Details Process for stereoselectively reducing indole derivatives Process for stereoselectively reducing indole derivatives

1978-07-26

1980-08-12

Rotman, Alan L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 85, 546 86, 546 87, 26032611R, 2603265B, 2603269, C07D47104, C07D47114

Patent

active

042174546

ABSTRACT:
Process for the stereoselective reduction of certain amino-substituted indoles and amino-substituted indole-containing structures to trans-dihydroindoles comprising the sequential steps of (1) reacting a strong acid addition salt of such an indole with a borohydride in an appropriate solvent in the absence of acid, and (2) acidifying the step (1) reaction product by which it is reduced and hydrolyzed to form the corresponding trans-dihydroindole. Many dihydroindoles so produced, for example, the trans-2-(adamantylemethyl)-=2,3,4,4a,5,9b-hexahydro-5-phenyl-1H-pyrido[4,3 -b]indole, are useful as pharmaceutical materials, such as tranquilizers.

REFERENCES:
patent: 3890327 (1975-06-01), Berger
patent: 3932650 (1976-01-01), Adams
patent: 3989717 (1976-11-01), Heath-Brown
patent: 3991199 (1976-11-01), Berger
patent: 4018930 (1977-04-01), Berger
patent: 4091102 (1978-05-01), Teller
patent: 4141980 (1979-02-01), Berger

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