Acetyl chloride → HCID 69489035, compound

Participants

Reaction Steps

To an ice-cooled solution of 0.070 g (0.104 mmol) of (3R,4R)-3-[1-(3-amino-propyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester [example 10(c)] and 0.013 g (0.125 mmol, 1.2 equiv.) of triethylamine in 1 ml of dichloromethane was added dropwise 0.009 g (0.114 mmol, 1.1 eqiuv.) of acetyl chloride. 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 ethyl acetate as the eluent and yielded 0.068 g (0.095 mmol, 91.3% of theory) of (3R,4R)-3-[1-(3-acetylamino-propyl)-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: 716 (M+H)+.

Provenance & Evidence