17,17-Bis(ethylendioxy)-6alpha-hydroxymethylandrostane → 17,17-Bis(ethylendioxy)-7beta-hydroxymethylandrostane

Participants

Reaction Steps

17,17-bis(ethylendioxy)-7α-hydroxymethylandrostane and 3,3:17,17-bis(ethylendioxy)-7β-hydroxymethylandrostane were prepared in 10% and 70% yield, respectively, from 3,3:17,17-bis(ethylendioxy)-7-methyleneandrostane (Prepn. 33, 2.9 g) by the procedure described above for the preparation of 3,3:17,17-bis(ethylendioxy)-6α-hydroxymethyl-androstane (Prepn. 14). The residue was purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40). 3,3:17,17-bis(ethylendioxy)-7α-hydroxymethylandrostane 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.85-3.75 (8H, m), 3.67 (2H, m), 3.34 (1H, t), 2.00-0.90 (21H, m), 0.87 (3H, s), 0.81 (3H, s) 3,3:17,17-bis(ethylendioxy)-7β-hydroxymethylandrostane 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.90-3.75 (8H, m), 3.58 (2H, m), 3.31 (1H, t), 2.00-1.10 (21H, m), 0.84 (3H, s), 0.81 (3H, s).

Provenance & Evidence