3beta,17beta-Dihydroxyandrostan-6-one → 6,6-Ethylendioxyandrostane-3beta,17beta-diol

HRID 1912670Notes

Reaction equation

HRID 1912670 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[CH:4]([C:5](=[O:22])[CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[OH:21])[CH2:3]1.[CH2:23]1[CH2:36]OC23OCCOC2([C@]2(CC[C@H]4[C@@H](CC=C5[C@]4(C)CCCC5)[C@@H]2C3)C)[O:24]1>>[CH2:36]1[CH2:23][O:24][C:5]2([CH:4]3[C@:17]([CH3:20])([CH2:18][CH2:19][C@H:2]([OH:1])[CH2:3]3)[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C@@H:11]([OH:21])[CH2:10][CH2:9]4)[CH2:6]2)[O:22]1

Participants

3

Reactant 2

HCID 121589203beta,17beta-Dihydroxyandrostan-6-oneHCID 86651495HCID 86651495, compound

Product 1

HCID 691334116,6-Ethylendioxyandrostane-3beta,17beta-diolYield 70%

Procedure

6,6-Ethylendioxyandrostane-3β,17β-diol was prepared in 70% yield from 3β,17β-dihydroxyandrostan-6-one by the procedure described above for the preparation of 3,3:17,17-bis(ethylendioxy)-5-androstene (Prepn. 5). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness to give 6,6-ethylendioxyandrostane-3β,17β-diol. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.45 (d, 1H), 4.41 (d, 1H), 3.90-3.57 (m, 4H), 3.41 (m, 1H), 3.29 (m, 1H), 1.87-0.53 (m, 20H), 0.84 (s, 3H), 0.60 (s, 3H).

Workup

  1. customdescribed above for the preparation of 3,3
  2. washThe combined organic extracts were washed with H2O
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customto give 6,6-ethylendioxyandrostane-3β,17β-diol

Sources & evidence

ORD record
ord-fcafa924f39f41739a0fca43610536a4
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

Loading…