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0 °C

To a −78° C. mixture of 4a (100 mg, 0.26 mmol) in Et2O (3 mL) was slowly added LAH (0.26 mL, 0.26 mmol, 1.0 M solution in Et2O). The resulting mixture was allowed to warm to 0° C. and then quenched by addition of a chilled saturated aq. solution of potassium sodium tartrate. The aqueous layer was extracted 3 times with Et2O. The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by flash chromatography (hexane-EtOAc 75:25) to yield 5a (80 mg, 90%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ0.27 (s, 9H), 0.91 (t, J=7.5 Hz, 3H), 2.43 (q, J=7.5 Hz, 2H), 3.43 (s, 3H), 4.01 (s, 3H), 4.33 (d, J=6.9 Hz, 2H), 4.53 (s, 2H), 4.69 (s, 2H), 5.61 (t, J=6.9 Hz, 1H), 6.87 (s, 1H); 13C NMR (75 MHz, CDCl3) δ−1.97, 13.01, 25.27, 53.37, 55.32, 58.79, 61.58, 95.91, 115.9, 122.3, 128.7, 142.36, 152.2, 162.3, 164.3; IR (film, NaCl, cm−1) 3388, 2949, 1576, 1450, 1340, 1042, 854; LRMS (70 eV, EI) m/z (rel int %) 339 (M+), 324, 308, 294, 277, 262 (100), 248, 232, 218, 188, 174, 117, 89, 73, 59. HRMS m/z calcd for C17H29NO2Si (M+) 339.1866, found 339.1861.

1. customquenched by addition of a chilled saturated aq. solution of potassium sodium tartrate
2. extractionThe aqueous layer was extracted 3 times with Et2O
3. dry with materialThe combined organic extracts were dried over MgSO4
4. concentrationconcentrated under reduced pressure
5. customThe crude product was purified by flash chromatography (hexane-EtOAc 75:25)