Sodium Sulfate → HCID 21255871, compound

Participants

Reaction Steps

To a solution of methyl 3-t-butyldiphenylsilyloxy-2-thioacetoxypropionate (example 40) (14.3 g, 34.4 mmol) in dichloromethane (1.0 L) was added diisobutylaluminium hydride (96 mL of 1.5M solution in toluene, 144 mmol, 4.2 eq) at -78° C. The solution was strirred at -78° C. for 1 hr and at -50° C. for another 1.5 hr. Sodium sulfate decahydrate (15 g) was added and the mixture was warmed at room temperature for 2 hr. Acetone was added and the solution was stirred overnight. Anhydrous sodium sulfate was added and the solution was strirred for 30 min and filtered over celite. The solid was washed several times with acetone and the solvents were evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexane and ethyl acetate (85:15) to give the desired compound (4.25 g) in 36% yield. 1H NMR (300 MHz, CDCl3) δ: 1.08 (s, 9H, t-butyl), 1.56 (d, 1H, J=9.9 Hz, SH), 3.02 (m, 1H, H-2), 3.7-3.93 (m, 4H, CH2), 7.43 and 7.67 (m, 10H, Ar-H).

Provenance & Evidence