17,17-Bis(ethylendioxy)-6-methyleneandrostane → HCID 86635586, compound

HRID 1912716Notes

Reaction equation

HRID 1912716 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]([C:16](=O)[CH2:17][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.[CH2:29]1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](CC(=C)C5[C@]4(C)CCCC5)[C@@H]2C3)C)O1>>[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]([C:16](=[CH2:29])[CH2:17][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

Participants

3

Reactant 2

HCID 6753593917,17-Bis(ethylendioxy)-6-methyleneandrostaneHCID 6895071317,17-Bis(ethylendioxy)androstan-7-one

Product 1

HCID 86635586HCID 86635586, compoundYield 85%

Procedure

17,17-Bis(ethylendioxy)-7-methyleneandrostane was prepared in 85% yield from 3,3:17,17-bis(ethylendioxy)androstane-7-one (Prepn. 42) by the procedure described above for the preparation of 3,3:17,17-bis(ethylendioxy)-6-methyleneandrostane (Prepn. 8). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 4.67 (m, 1H), 4.60 (m, 1H), 3.86 (m, 8H), 2.12-0.75 (m, 20H), 0.97 (s, 3H), 0.86 (s, 3H).

Workup

  1. washThe combined organic extracts were washed with H2O
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-f7e0476cc38b49c889a3e0076b19f90a
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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