Reaction Steps
A stirred solution of alcohol 61 (90 mg, 0.35 mmol) and NaI (104 mg, 0.69 mmol) in MeCN (3 mL) under argon at room temperature was treated with ClSiMe3 (0.11 mL, 0.87 mmol), resulting in the formation of fine precipitate. After stirring for 10 minutes, Et2NH (0.14 mL, 1.39 mmol) was added and the reaction mixture was left to stir for a further 15 h. CH2Cl2 (10 mL) was added and the mixture washed with H2O (3×5 mL), brine (1×5 mL), dried over Na2SO4, filtered, and all volatiles were removed in vacuo. The crude product was dissolved in EtOAc and filtered through a pad of silica gel, eluting with 95:3:2 EtOAc/i-PrOH/Et3N. Evaporation of the filtrate afforded amine 64 (103 mg, 95%) as an orange oil: Rf=0.25 (silica, 95:3:2 EtOAc/i-PrOH/Et3N); IR (KBr, neat) vmax 3093, 2968, 2937, 2819, 2780, 1487, 1452, 1421 cm−1; 1H NMR (300 MHz, CDCl3) δ 4.13 (s, 5H), 3.97 (t, 1H, J=1.8 Hz), 3.89 (t, 1H, J=2.0 Hz), 3.86 (t, 1H, J=2.4 Hz), 3.75 (AB d, 1H, J=13.2 Hz), 3.12 (AB d, 1H, J=12.9 Hz), 2.68 (s, 6H), 2.61 (dq, 2H, J=13.8, 6.9 Hz), 2.41 (dq, 2H, J=13.0, 7.1 Hz), 0.98 (t, 6H, J=7.2); 13C NMR (75 MHz, CDCl3) δ 113.7, 76.6, 68.5, 68.3, 61.7, 56.9, 52.2, 45.9, 44.9, 11.2; EIMS [m/z (%)] 314 (M+, 100), 241 (39), 121 (38); HRMS (EI) calcd for C17H26N256Fe: 314.1445. Found 314.1445.
