Reaction Steps
A 1 M solution of borane-methyl sulfide complex in dichloromethane (27 mL, 27 mmol) was added dropwise to a stirred solution of the olefin 14 (21 g, 80.36 mmol), prepared according to Example 12, in hexane (60 mL) at 0° C. The mixture was stirred for 3 h at room temperature, then cooled to 0° C., and then absolute ethanol (15 mL) was added dropwise, followed by 15% NaOH (15 mL) and 30% H2O2 (15 mL). The reaction mixture was heated at reflux for 1 h. cooled to room temperature, and poured into water (200 mL). The organic layer was separated, and the aqueous layer was extracted with ether (3×75 mL). The organic layers were combined, dried over MgSO4, and concentrated under reduced pressure. The crude product was chromatographed on a silica gel column, eluting with 2% methanol in ether, to give the alcohol 15 (16.8 g, 74.6%) as a viscous liquid. IR (KBr)νmax 3442, 3034, 2952, 2878, 1458, 1407, 1364, 1206, 1103, 846, 742, 698 cm−1; 1HNMR (CDCl3) δ 1.36-1.39 (m, 1 H), 1.53-1.64 (m, 4 H), 1.79-1.90 (m, 3 H), 3.53-3.59 (m, 4 H), 3.79-3.92 (m, 4 H), 4.49 (s, 2H), 4.78 (d, J=3.6 Hz, 1 H), 7.25-7.32 (m, 5 H); 13CNMR (CDCl3) δ 25.38, 29.23, 30.17, 38.19, 62.76, 64.78, 64.84, 68.52, 72.72, 106.49, 127.39, 127.56, 128.23, 138.54: mass spectrum (EI), m/z (rel intensity) 280 (M+.0.02), 235(2.1), 220 (14), 219 (84), 218 (69), 172 (15), 146 (23), 127 (15), 91 (35), 84 (9), 73 (10), 65 (5.5).
