Methanol → HCID 69488943, compound

Participants

Reaction Conditions

Reaction Steps

To an ice cooled solution of 0.240 g (0.319 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 3 ml of absolute methanol was added 0.0 17 g (0.383, 1.2 equiv.) of sodium hydride (55% suspension in mineral oil). The reaction was then stirred for 6 h at 50° C., allowed to cool 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 v/v mixture of hexane and ethyl acetate as eluent to yield 0.143 g (0.208 mmol, 65.2% of theory) of (3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-[1-(3-methoxy-propyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester as a yellow oil; MS: 689 (M+H)+.

Provenance & Evidence