Ammonium Chloride → 3-(1-Phenyl-ethylamino)-butan-2-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.445 ml (5 mmol) cis-2,3-dimethyl-oxirane in 5 ml tetrahydrofuran was added at room temperature 0.26 g (1 mmol) magnesium bromide diethyl etherate. The mixture was treated under argon with stirring with 0.67 ml (5.5 mmol) (S)-(−)-1-phenyl-ethylamine. The yellow suspension was heated at 90° C. in a closed container for 110 hours, whereby after 21 and 64 hours 0.25 ml and 0.122 ml respectively of cis-2,3-dimethyl-oxirane was added. The reaction mixture was cooled to room temperature and stirred vigorously with 5 ml of 5N aqueous ammonium chloride solution for 10 minutes. The organic phase was separated, dried over 2 g of sodium sulfate, filtered and evaporated in a rotary evaporator to obtain 0.58 g of 3-(1-phenyl-ethylamino)-butan-2-ol as a mixture of diastereoisomers as a brown oil. The oily residue was separated by chromatography on a silica gel column using ethyl acetate as the eluent to obtain the two diastereoisomers A and B as yellowish oils.

Provenance & Evidence