3beta-Hydroxy-5alpha,6alpha-epoxyandrostane-17-one → HCID 86651494, compound

HRID 1912667Notes

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]([CH2:16][CH:17]=[C: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.[OH:28][C@H]1CC[C@@]2(C)[C@]3(O[C@H]3C[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC2=O)C1>>[CH2:11]1[CH2:10][O:9][C:8]23[O:13][CH2:14][CH2:1][O:2][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([CH2:16][C@@H:17]5[O:28][C@@:18]65[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]6)[C@@H:6]2[CH2:7]3)[CH3:5])[O:12]1

Participants

Reactant 2

HCID 70751553beta-Hydroxy-5alpha,6alpha-epoxyandrostane-17-one

HCID 86651495HCID 86651495, compound

Product 1

HCID 86651494HCID 86651494, compoundYield 45%

Procedure

17,17-Bis(ethylendioxy)-5α,6α-epoxyandrostane was prepared in 45% yield from 3,3:17,17-bis(ethylendioxy)-5-androstene by the procedure described above for the preparation of 3β-hydroxy-5α,6α-epoxyandrostan-17-one (Prepn. 4). The crude product was purified by flash chromatography (SiO2, n-hexane/EtOAc 80/20). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.92-3.75 (m, 8H), 2.68 (m, 1H), 2.56 (d, 1H), 1.99-1.06 (m, 18H), 1.09 (s, 3H), 0.78 (s, 3H).

Workup

customThe crude product was purified by flash chromatography (SiO2, n-hexane/EtOAc 80/20)

Sources & evidence

ORD record: ord-b3b83fd6236e42e2952abc4602da9821
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609644B2

Reaction notes

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