Deoxycorticosterone → Deoxycorticosterone acetate

HRID 979422Notes

Reaction equation

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

Participants

Reactant 2

HCID 6166Deoxycorticosterone

HCID 312751,4-Dioxane

Product 1

HCID 5952Deoxycorticosterone acetateYield 89%

Procedure

1.16 g (3.5 mmoles) of 4-pregnene-3,20-dione-21-ol [prepared as described in Step (c) above] are acetylated as described in Example 2 to give 1.16 g (89% yield) of the aimed product, m.p.: 156°-158° C., [α]D =+174° (c=1.0 in dioxane).

Sources & evidence

ORD record: ord-f428ed2e43094318850dfe7b99c22288
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04668437

Reaction notes

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