17,17-Bis(ethylendioxy)-6alpha-vinylandrostane → 17,17-Bis(ethylendioxy)-6alpha-(2-hydroxyethyl)androstane

HRID 1912677Notes

Reaction equation

HRID 1912677 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]([CH2:16][C@H:17]([CH:28]=[CH2:29])[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@@H](CO)C5[C@]4(C)CCCC5)[C@@H]2C3)C)[O:31]1>>[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]([CH2:16][C@H:17]([CH2:28][CH2:29][OH:31])[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

3

Reactant 2

HCID 8663557417,17-Bis(ethylendioxy)-6alpha-vinylandrostaneHCID 8665149717,17-Bis(ethylendioxy)-6beta-hydroxymethylandrostane

Product 1

HCID 8663557517,17-Bis(ethylendioxy)-6alpha-(2-hydroxyethyl)androstaneYield 96%

Procedure

17,17-Bis(ethylendioxy)-6α-(2-hydroxyethyl)androstane was prepared in 96% yield from 3,3:17,17-bis(ethylendioxy)-6α-vinylandrostane (Prepn. 11) by the procedure described above for the preparation of 3,3:17,17-bis(ethylendioxy)-6β-hydroxymethylandrostane (Prepn. 9). The crude was purified by flash chromatography (SiO2, n-hexane/acetone 80/20). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.25 (t, 1H), 3.86-3.70 (m, 8H), 3.35 (m, 2H), 1.91-0.42 (m, 23H), 0.75 (s, 3H), 0.74 (s, 3H).

Workup

  1. customThe crude was purified by flash chromatography (SiO2, n-hexane/acetone 80/20)

Sources & evidence

ORD record
ord-57e43c28166243ca8288574c007a3b19
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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