HCID 67536381, compound → 6alpha-Hydroxymethylandrostane-3,17-dione

HRID 42086Notes

Reaction equation

HRID 42086 reaction equation
C1CO[C:8]23OCCO[C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([CH2:16][C@H:17]([CH2:28][OH: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.C=C1C2[C@](C)(CCC(=[O:49])C2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C(=O)CC3)C1>>[OH:29][CH2:28][C@@H:17]1[CH:18]2[C@:23]([CH3:24])([CH2:22][CH2:21][C:20](=[O:49])[CH2:19]2)[C@@H:25]2[C@H:15]([C@H:6]3[C@@:4]([CH2:27][CH2:26]2)([CH3:5])[C:3](=[O:2])[CH2:8][CH2:7]3)[CH2:16]1

Participants

3

Reactant 2

HCID 67536381HCID 67536381, compoundHCID 8663556417,17-Bis(ethylendioxy)-6alpha-hydroxymethylandrostane

Product 1

HCID 690108246alpha-Hydroxymethylandrostane-3,17-dioneYield 85%

Procedure

The title compound II-ad was prepared in 85% yield from 3,3:17,17-bis(ethylendioxy)-6α-hydroxymethylandrostane by the procedure described above for the preparation of 6-methyleneandrostane-3,17-dione (II-ac, Prepn. 13). The combined organic extracts were washed with H2O, dried and evaporated to dryness. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.50 (3H, m), 2.52-0.74 (21H, m), 1.11 (3H, s), 0.88 (3H, s).

Workup

  1. washThe combined organic extracts were washed with H2O
  2. customdried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-97b3d73ec7b4460087489cab9ff24b28
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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