Hydrochloric Acid → (3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-piperidine

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Reaction Conditions

Reaction Steps

2.92 g (4.73 mmol) of (3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-piperidine-1-carboxylic acid tert-butylester were dissolved in 63 ml of abs. methanol, then 63 ml (126 mmol) of hydrochloric acid in methanol (2.0 molar) were added at room temperature. After stirring for 150 minutes at 50° C., the reaction mixture was poured into 150 ml ice-cold 5% sodium hydrogen carbonate solution and the product was extracted five times with 100 ml methylene chloride. The combined organic phases were washed twice with 50 ml distilled water, dried over magnesium sulphate, filtered and concentrated. The crude product (2.9 g, yellow oil) was chromatographed on silica gel with methylene chloride/methanol/28%ammonium hydroxide solution 14:1:0.1 v/v/v to yield 1.90 g (77.7% of theory) of (3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-piperidine as a slightly yellow resin; MS: 517 (M+H)+.

Provenance & Evidence