Sodium Hydroxide → (R)-2-(Methylamino)-2-phenylethanol

Participants

Reaction Steps

Lithium aluminum hydride (1.84 g, 43 mmol) was suspended in 30 ml of tetrahydrofuran and cooled in an ice-bath. A solution of (R)-methylamino-phenyl acetic acid (1.0 g, 6 mmol) in 10 ml of tetrahydrofuran was slowly added over a period of 20 minutes. The resulting mixture was stirred for 1 hour at 0°, 4 hours at room temperature and then refluxed overnight. The mixture was cooled and carefully hydrolysed by addition of 50 ml 15% aqueous sodium hydroxide. Extraction with ethyl acetate gives a crude oil which was purified by chromatography on silica gel using heptane/ethyl acetate 9:1 v/v to give the title compound as a slightly yellowish oil (0.36 g, yield=39%).

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