Ammonium Chloride → HCID 44252105, compound

Participants

Reaction Steps

A 2 M solution of benzylmagnesium chloride in tetrahydrofuran (6.00 ml, 12 mmol) was added dropwise to a solution of 4-dimethylamino-4-(3-fluorophenyl)cyclohexanecarbaldehyde (1.49 g, 5.97 mmol) in anhydrous tetrahydrofuran (30 ml), while cooling with ice. The mixture was stirred at room temperature for 2 d and saturated ammonium chloride solution (30 ml) was then added, while cooling with ice. The tetrahydrofuran was removed i. vac. and the residue was brought to pH 8 with 4 M sodium hydroxide solution. The aqueous suspension was extracted with diethyl ether (3×30 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac. The crude product (2.18 g) was purified by flash chromatography with methylene chloride/methanol [95:5+1% NH3 (32% in H2O)]. The impure polar diastereoisomer (500 mg) was purified again by flash chromatography with methylene chloride/methanol [95:5+1% NH3 (32% in H2O)].

Provenance & Evidence