Potassium Carbonate → (3RS,4RS)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(1-methoxycarbonylmethyl-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 0.133 g (0.189 mmol) of (3RS,4RS)-3-(1-ethoxycarbonylmethyl-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester [example 2(d)] in 5 ml of methanol was treated with 0.10 g (0.72 mmol) of anhydrous potassium carbonate. The suspension was stirred for 1 h at 25° C. The salts were filtered off, the filtrate was concentrated. 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, and yielded 0.060 g (0.087 mmol, 46.1% of theory) of (3RS,4RS)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(1-methoxycarbonylmethyl-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester as yellow oil; MS: 689 (M+H)+.

Provenance & Evidence