Water → (R)-3-(1-(naphthalen-1-yl)ethylamino)-1-(3-(trifluoromethyl)phenyl)propan-1-ol hydrochloride

Participants

Reaction Conditions

Reaction Steps

(R)-3-(1-(naphthalen-1-yl)ethylamino)-1-(3-(trifluoromethyl)phenyl)propan-1-one hydrochloride (V) (15.95 g, 39.104 mmol) is suspended in cold methanol (50 ml) at −10° C. and, subsequently, a solution of sodium borohydride (0.75 g, 19.610 mmol), 30% w/w aqueous sodium hydroxide (5.74 g, 43.014 mmol) and water (5 ml) is added slowly in order to keep the internal temperature below 0° C. The reaction mixture is stirred at 0° C. for 0.5 hrs and then quenched by addition of 30% w/w aqueous hydrochloric acid up to pH=1, followed by water (40 ml), and allowed to reach room temperature. The so-formed thick suspension is heated up to 50° C., stirred for 20 minutes and then cooled down to 5° C. The precipitate is filtered, washed with a 9:1 vol/vol water/methanol mixture (10 ml) and dried at 50° C. under vacuum. 14.69 g (35.841 mmol) of high quality (R)-3-(1-(naphthalen-1-yl)ethylamino)-1-(3-(trifluoromethyl)phenyl)propan-1-ol hydrochloride (IXa) are obtained (yield: 91.7%; white powder).

Provenance & Evidence