Acetic Acid → Androstenediol diacetate

HRID 273691Notes

Reaction equation

[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:24][C:25](=[O:27])[CH3:26])[CH2:6]1)(=[O:3])[CH3:2].C(O)(=[O:30])C>>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:24][C:25](=[O:27])[CH3:26])[CH2:6]1)(=[O:3])[CH3:2].[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][C:9](=[O:30])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:24][C:25](=[O:27])[CH3:26])[CH2:6]1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 176Acetic Acid

HCID 102205Androstenediol diacetate

Product 2

HCID 102205Androstenediol diacetate

HCID 9886600(3S,8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-7-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate

Procedure

βAET was synthesized using 3β,17β- diacetoxyandrost-5-ene as a starting material. Chromic oxide oxidation of 3β,17β-diacetoxyandrost-5-ene in glacial acetic acid by the method of Butenandt (op. cit.) gave 3β,17β-diacetoxyandrost-5-en-7-one, (III), the intermediate for preparation of (I). Aluminum isopropoxide reduction of (III) in isopropanol by the method of Butenandt gave (I).

Workup

customβAET was synthesized

Sources & evidence

ORD record: ord-f86041a7c9664c069aa7dd46a6156922
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05387583

Reaction notes

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