1-[(Benzyloxy)carbonyl]-1,2,3,4-tetrahydroquinoline-3-carboxylic acid → Benzyl 3-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline-1-carboxylate

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Reaction Steps

14.0 g of N-benzyloxycarbonyl-3(R,S)-carboxy-1,2,3,4-tetrahydroquinoline are stirred in 400 ml of tetrahydrofuran with 9.0 ml of 10M borane-dimethylsulfide complex at 25° C. for 16 h. The reaction mixture is diluted several times with methanol and evaporated. The crude product is recrystallized from ethyl acetate/hexane: mp 62°-4° C.; Rf (X)=0.50; FAB-MS: (M+H)+ =298; anal. calc. for C18H19NO3 : C 72.71%, H 6.44%, N 4.71%; found C 72.84%, H 6.35%, N 4.75%.

Provenance & Evidence