Potassium Cyanide → HCID 69489276, compound

Participants

Reaction Conditions

Reaction Steps

To a well stirred solution of 0.200 g (0.266 mmol) of crude (3R,4R)-3-[1-(3-methanesulfonyloxy-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(a)] in 1.8 ml of absolute N,N-dimethylformamide was added 0.026 (0.399 mmol, 1.5 equiv.) of potassium cyanide. After stirring for 45 min at 50° 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 2:1 mixture of hexane and ethyl acetate as the eluent to yield 0.130 g (0.190 mmol, 71.4% of theory) 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 as a light yellow oil; MS: 684 (M+H)+.

Provenance & Evidence