HCID 69489276, compound → HCID 69489222, compound

Participants

Reaction Conditions

Reaction Steps

To a well stirred solution of 0.130 g (0.190 mmol) of (3R,4R)-3-[1-(3-cyano-propyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester in 0.5 ml of absolute THF was added dropwise 1 ml of a 1M solution of borane-THF complex in THF. After stirring for 3 h at 70° C., the reaction was allowed to warm to room temperature, poured into 50 ml of an ice/water mixture and extracted three times with 50 ml of ethyl acetate. The combined organic phases were washed twice with 20 ml of water, evaporated under reduced pressure and dried in a high vacuum. The thus-obtained crude product was purified by chromatography on silica gel using a 140:10:1 v/v/v mixture of dichloromethane/methanol/28% ammonium hydroxide solution as the eluent to yield 0.090 g (0.131 mmol, 68.9% of theory) of (3R,4R)-3-[1-(4-amino-butyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester as a light yellow oil; MS: 688 (M+H)+.

Provenance & Evidence