Ammonium Chloride → HCID 15855304, compound

Participants

Reaction Conditions

Reaction Steps

Cuprous cyanide (5 mg) was placed in a flask which was flushed with N2 gas. Anhydrous tetrahydrofuran (0.5 ml) was added, and the mixture was cooled under N2 to 30° C. A solution of benzylmagnesium chloride (0.18 ml, 1.0M in diethyl ether) was added, and the mixture was stirred for 10 min to produce a yellow slurry. A solution of 30 mg (0.073 mmol) of the resultant compound of Example 7 in 1 ml of anhydrous tetrahydrofuran was subsequently added, and the resulting solution was stirred and allowed to warm to -10° C. over a period of 30 min. After addition of aqueous ammonium chloride, the mixture was extracted with ethyl acetate, washed with saturated brine, dried over Na2SO4, and concentrated in vacuo. Chromatography on silica gel using 6:1 hexane:ethyl acetate provided 25 mg (84%) of the desired compound (Rf 0.71, 2:1 hexane:ethyl acetate). 1H NMR (CDCl3) δ 1.41 (s, 9 H), 2.2-2.3 (m, 3 H), 3.04 (dd, J=13, 7 Hz, 1 H), 3.25 (q, J=7 Hz, 1 H), 3.61 (s, 3 H), 4.37 (m, 2 H), 5.39 (dd, J=15, 5 Hz, 1 H), 5.55 (dd, J=15, 8 Hz, 1 H), 7.05-7.15 (m, 4 H), 7.2-7.3 (m, 6 H). Mass spectrum: (M+NH4)+ =427.

Provenance & Evidence