HCID 13519092, compound → HCID 56637783, compound

HRID 652274Notes

Reaction equation

HRID 652274 reaction equation
C([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:28])[C@@H:18]4[CH2:27][C@@H:19]42)[C:14](=[CH2:29])[CH2:13]3)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=O)C>CO.[OH-].[Na+]>[OH:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:28])[C@@H:18]4[CH2:27][C@@H:19]42)[C:14](=[CH2:29])[CH2:13]3)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7]

Participants

4

Reactant 1

HCID 13519092HCID 13519092, compound

Product 1

HCID 56637783HCID 56637783, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Under argon, 500 mg of 17α-acetoxy 1α,2α-methylene-6-methylene-4-pregnene-3,20-dione is agitated for 16 hours in 30 ml of methanol and 16 ml of 5% sodium hydroxide solution. The mixture is poured on an ice water-sodium chloride solution and worked up as usual. The crude product is purified on 50 g of silica gel with a hexane-acetone gradient, thus isolating 380 mg of 17α-hydroxy-1α,2α-methylene-6-methylene-4-pregnene-3,20-dione.

Workup

  1. customThe crude product is purified on 50 g of silica gel with a hexane-acetone gradient

Sources & evidence

ORD record
ord-6a8b2ae3c0f54d0f92f646918a6b738c
Source dataset
uspto-grants-1987_06
Patent number
US04670427

Reaction notes

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