Potassium Carbonate → HCID 10016807, compound

Participants

Reaction Conditions

Reaction Steps

The TBDMS-protected compound of Example 1 (900 mg, 2.88 mmol) was dissolved in 12 mL of methylene chloride. The solution was cooled to -78° C., and a 1M solution of diisobutylaluminum hydride in hexanes (11.5 mL, 11.5 mmol) was added. The reaction mixture was stirred at -78° C. for 4 hr. A saturated solution of K2CO3 was added to quench the reaction. The aqueous layer was extracted with chloroform. The combined organic layers were washed with water and brine and dried over MgSO4. The solvent was evaporated in vacuo, and the residue was chromatographed using methanol as eluent to give 650 mg of the title alcohol 3 (79% yield): IR (thin film) 3453, 2947, 2899, 2857, 1472, 1252, 1098, 837 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ 4.12-3.85 (m, 3H), 3.45-3.37 (m, 1H), 3.21-3.17 (m, 1H), 2.22 (s, 3H), 2.20-1.50 (m, 8H), 0.88 (s, 9H), 0.04 (s, 6H); 13C NMR (CDCl3, 75.46 MHz) δ 66.9, 65.7, 63.6, 61.5, 46.5, 41.2, 40.6, 26.0, 25.4, 18.3, 6.6, 6.3; mass spectrum m/z 285 (M+), 228, 154, 126, 83; HRMS (FAB) calcd for C15H32NO2Si (MH+) 286.2194, found 286.2215.

Provenance & Evidence