m-Chloroperbenzoic acid → 17,17-(Ethylendioxy)-5alpha-hydroxyandrostane-3-one

HRID 1912725Notes

Reaction equation

HRID 1912725 reaction equation
[OH:1][C@:2]12[CH2:19][C:18](=[O:20])[CH2:17][CH2:16][C@:15]1([CH3:21])[C@@H:14]1[C@H:5]([C@H:6]3[C@@:10]([CH2:12][CH2:13]1)([CH3:11])[C:9](=[O:22])[CH2:8][CH2:7]3)[CH2:4][CH2:3]2.[CH2:23]1[CH2:46]OC2(CC[C@H]3[C@H]4[C@H](CC[C@]23C)[C@]2(C)C(C[C@@H](O)CC2)=CC4)[O:24]1.C1C=C(Cl)C=C(C(OO)=O)C=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[CH2:46]1[CH2:23][O:24][C:9]2([CH2:8][CH2:7][C@H:6]3[C@H:5]4[C@H:14]([CH2:13][CH2:12][C@:10]23[CH3:11])[C@:15]2([CH3:21])[C@:2]([OH:1])([CH2:19][C:18](=[O:20])[CH2:17][CH2:16]2)[CH2:3][CH2:4]4)[O:22]1

Participants

5

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 118237795-Androsten-3beta-ol-17-one ethyleneketalHCID 14135097HCID 14135097, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 6913402717,17-(Ethylendioxy)-5alpha-hydroxyandrostane-3-oneYield 55%

Procedure

Following the procedures described for the preparation of 5α-hydroxyandrostane-3,17-dione (II-ad, Prepn. 4), starting from 17,17-(ethylendioxy)-5-androsten-3β-ol after epoxidation with mCPBA, reduction with LAH, and oxidation with IBX, 17,17-(ethylendioxy)-5α-hydroxyandrostane-3-one was obtained in 55% yield. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ4.29 (s, 1H), 3.78 (m, 4H), 2.69-1.10 (m, 21H), 1.07 (s, 3H), 0.76 (s, 3H).

Sources & evidence

ORD record
ord-c98abe13784f4c11ab609b0899c969dc
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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