Bromide ion → HCID 89526867, compound

Participants

Reaction Conditions

Reaction Steps

While under a nitrogen atmosphere, a solution of tert-Butyl-biphen-4-ylmethyl-{(1S,3R)-3-(methoxy(methyl)carbamoyl)-cyclopentyl}-carbamate (1.2 g, 2.74 mmol), in tetrahydrofuran (20 mL) was cooled to 0° C. and treated with 3-butenylmagnesiun bromide (0.5 M in THF, 13.7 mL, 6.85 mmol) in a drop wise manner. The solution was stirred for 1 hour at 0° C. then allowed to warm to room temperature overnight. The resulting solution was poured into water, acidified to pH 3-4 with 1 N hydrochloric acid, and extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Purification by flash column chromatography (silica gel, 0-30% ethyl acetate in heptane) gave tert-Butyl-biphen-4-ylmethyl-{(1S,3R)-3-pent-4-enoylcyclopentyl}-carbamate as a colorless oil (1.12 g, 94%); 1H NMR (CDCl3, 400 MHz) δ 7.62 d, J=7.5 Hz, (2H), 7.56 (d, J=7.5 Hz, 2H), 7.46 (t, J=7.5 Hz, 2H), 7.36 (m, 1H), 7.28 (m, 2H), 5.80 (m, 1H), 5.01 (m, 2H), 4.48 m, (3H), 2.92 (m, 1H), 2.54 (m, 2H), 2.37 (m, 2H), 2.04 (m, 1H), 1.74-1.94 (m, 4H), 1.48-1.66 (m, 1H), 1.43 (s, 9H).

Provenance & Evidence