Water → Cyproterone acetate

HRID 1285096Notes

Reaction equation

HRID 1285096 reaction equation
[C:1]([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@H:14]([Cl:29])[C@H:13]3O)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OC)(OC)OC.O>ClCCl>[C:1]([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]([Cl:29])=[CH:13]3)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 13423627[(1S,2S,3S,5R,9S,10S,11R,12S,15R,16S)-15-acetyl-9-chloro-10-hydroxy-2,16-dimethyl-6-oxo-15-pentacyclo[9.7.0.02,8.03,5.012,16]octadec-7-enyl] acetate

Product 1

HCID 9880Cyproterone acetateYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 g of 17α-acetoxy-6β-chloro-7α-hydroxy-1α,2α-methylene-4-pregnene-3,20-dione is mixed in 25 ml of dichloromethane with 0.1 g of p-toluenesulfonic acid and 3.0 ml of trimethyl orthoformate. The mixture is allowed to stand for 4 hours at 0° C., mixed with 20 ml of water and stirred for 15 minutes. Then the organic phase is separated, dried with sodium sulfate and concentrated in vacuo. Thus, 4.8 g of 17α-acetoxy-6-chloro-1α,2α-methylene-4,6-pregnadiene-3,20-dione with a melting point of 202° to 205° C. (80% purity) is obtained.

Workup

  1. customThen the organic phase is separated
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6025f50579b4731afb2d98ae8bbc762
Source dataset
uspto-grants-1986_01
Patent number
US04565657

Reaction notes

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