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

HRID 42117Notes

Reaction equation

HRID 42117 reaction equation
[CH2:1]1[CH2:14][O:13][C:8]23[O:9][CH2:10][CH2:11][O:12][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([C@H:16]([CH2:28][OH:29])[CH2:17][CH:18]5[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:2]1.C1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](C(=C)CC5[C@]4(C)CCCC5)[C@@H]2C3)C)O1.C1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](C[C@H](CO)C5[C@]4(C)CCCC5)[C@@H]2C3)C)O1>>[CH2:11]1[CH2:10][O:9][C:8]23[O:13][CH2:14][CH2:1][O:2][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([C@@H:16]([CH2:28][OH:29])[CH2:17][CH:18]5[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:12]1

Participants

4

Reactant 3

HCID 8663556417,17-Bis(ethylendioxy)-6alpha-hydroxymethylandrostaneHCID 86635586HCID 86635586, compoundHCID 8663558817,17-Bis(ethylendioxy)-7alpha-hydroxymethylandrostane

Product 1

HCID 8663558717,17-Bis(ethylendioxy)-7beta-hydroxymethylandrostaneYield 70%

Procedure

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).

Workup

  1. customThe residue was purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40)

Sources & evidence

ORD record
ord-43683e7f220e466fb71b9ce8bed16c9e
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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