Benzyl mercaptan → HCID 25130205, compound

Participants

Reaction Conditions

Reaction Steps

A solution of n-BuLi (2.4 M in hexanes, 75 mL) was added slowly to a solution of benzyl mercaptan (25 mL, 210 mmol) in THF (250 mL) at 0° C. The resulting pale-yellow solution was stirred at 0° C. for 15 min prior to the introduction of (4R)-benzyl-3-({(7R,8R)-7-[(benzyloxy)methyl]-1,4-dioxaspiro[4.5]dec-8-yl}carbonyl)-1,3-oxazolidin-2-one (64.2 g, 138 mmol) as a solution in THF (250 mL). After 30 min, a solution of LiAlH4 (1.0 M in THF, 150 mL) was slowly added to the reaction mixture with continued stirring at 0° C. for 30 min. Ice water (15 mL) was then slowly added to destroy excess hydride followed by 6M HCl (110 mL) to pH 4. The mixture was extracted with two portions of ethyl acetate and the combined organics were washed with saturated aqueous NaCl and dried over Na2SO4. Concentration in vacuo and flash chromatography of the residue on silica gel eluting with 20/80 acetone/benzene afforded {(7R,8R)-7-[(benzyloxy)methyl]-1,4-dioxaspiro[4.5]dec-8-yl}methanol as a faint-yellow, thick syrup. 1H NMR (500 MHz, d6-acetone) δ 7.36 (4H, m), 7.29 (1H, m), 4.50 (2H, q, J=9.6 Hz), 3.90 (4H, s), 3.61 (1H, m), 3.52-3.42 (3H, m), 3.43 (1H, t, J= 5.5 Hz), 1.88-1.72 (4H, m), 1.55-1.41 (4H, m).

Provenance & Evidence