Sodium Bicarbonate → HCID 25142821, compound

Participants

Reaction Conditions

Reaction Steps

A 1.0 M solution of lithium tri-t-butoxy aluminum hydride in THF (6.27 mL, 6.27 mmol) was added in a dropwise manner to a solution of 3α-hydroxy-5α-androstan-17-thione (0.64 g, 2.09 mmol) in THF (60 mL) at 0° C. under N2. The solution was allowed to stir for 2 h at 0° C. and then another 2 h at room temperature. Saturated NaHCO3 (75 mL) was added and the slurry was extracted with CH2Cl2 (3×100 mL). The organics were combined, dried (MgSO4), and concentrated under reduced pressure. The resulting white solid was recrystallized from heptane to provide a white powder (0.61 g, 95%). mp. 169-170° C. 1H-NMR (300 MHz, CDCl3) δ 0.70 (s, 3H), 0.79 (s, 3H), 0.80-1.70 (m, 23H), 2.16-2.18 (m, 2H), 2.58-2.69 (dd, J=9, 18 Hz, 1H), 2.90-3.00 (dd, J=9, 9 Hz, 1H), 4.06 (m, 1H). Elemental Anal. for C19H32OS Calcd. C, 73.97; H, 10.45; S, 10.39. Found. C, 73.82; H, 10.73; S, 10.28.

Provenance & Evidence