17,17-(Ethylendioxy)-3-methylenandrostane-5alpha-ol → 17,17-(Ethylendioxy)-3alpha-hydroxymethylandrostane-5alpha-ol

HRID 1912727Notes

Reaction equation

HRID 1912727 reaction equation
C1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](C[C@@H](CO)C5[C@]4(C)CCCC5)[C@@H]2C3)C)[O:2]1.[CH2:30]1[CH2:54][O:53][C:32]2([CH2:37][CH2:36][C@H:35]3[C@H:38]4[C@H:48]([CH2:49][CH2:50][C@:33]23[CH3:34])[C@:46]2([CH3:47])[C@:41]([OH:52])([CH2:42][C:43](=[CH2:51])[CH2:44][CH2:45]2)[CH2:40][CH2:39]4)[O:31]1>>[CH2:54]1[CH2:30][O:31][C:32]2([CH2:37][CH2:36][C@H:35]3[C@H:38]4[C@H:48]([CH2:49][CH2:50][C@:33]23[CH3:34])[C@:46]2([CH3:47])[C@:41]([OH:52])([CH2:42][C@H:43]([CH2:51][OH:2])[CH2:44][CH2:45]2)[CH2:40][CH2:39]4)[O:53]1

Participants

3

Reactant 2

HCID 6913329517,17-(Ethylendioxy)-3-methylenandrostane-5alpha-olHCID 8665149717,17-Bis(ethylendioxy)-6beta-hydroxymethylandrostane

Product 1

HCID 6913332017,17-(Ethylendioxy)-3alpha-hydroxymethylandrostane-5alpha-olYield 98%

Procedure

Following the procedure described for the preparation of 3,3:17,17-bis(ethylendioxy)-6β-hydroxymethylandrostane (Prepn. 9) and starting from 17,17-(ethylendioxy)-3-methylenandrostane-5α-ol, 17,17-(ethylendioxy)-3α-hydroxymethylandrostane-5α-ol was obtained in 98% yield. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.44 (t, 1H), 3.81 (s, 1H), 3.76 (m, 4H), 3.58 (m, 1H), 3.39 (m, 1H), 1.91-0.97 (m, 22H), 0.87 (s, 3H), 0.74 (s, 3H).

Workup

  1. customdescribed for the preparation of 3,3

Sources & evidence

ORD record
ord-f7f23836d78845f2a0ff019503ced973
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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