Water → HCID 86733290, compound

HRID 1606478Notes

Reaction equation

HRID 1606478 reaction equation
[Br:1][C@H:2]1[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[C:18](=[O:23])[CH2:17][C@@:16]2([CH3:24])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:13](=[O:15])[CH3:14])[CH2:4][C@@H:3]1[OH:25].[C:26](OC(=O)C)(=[O:28])[CH3:27].O>N1C=CC=CC=1>[C:26]([O:25][C@@H:3]1[C@@H:2]([Br:1])[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[C:18](=[O:23])[CH2:17][C@@:16]2([CH3:24])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:13](=[O:15])[CH3:14])[CH2:4]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 86733291HCID 86733291, compound

Product 1

HCID 86733290HCID 86733290, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2β-Bromo-3α-hydroxy-5α-pregnane-11,20-dione (750 mg.) in pyridine (2 ml.) was treated with acetic anhydride (1 ml.) and the mixture was allowed to stand at room temperature overnight. It was then poured into water to give a white solid (720 mg.) which was recrystallised from methanol to give 3α-acetoxy-2β-bromo-5α-pregnane-11,20-dione (471 mg.) as white crystals, m.p. 154°-156°, [α]D + 128.5°.

Workup

  1. customto give a white solid (720 mg.) which
  2. customwas recrystallised from methanol

Sources & evidence

ORD record
ord-023018426ad944de95ee42be0cb8a951
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

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