m-Chloroperbenzoic acid → HCID 22788254, compound

HRID 267633Notes

Reaction equation

HRID 267633 reaction equation
[CH3:1][C@:2]12[CH2:19][C:18](=[O:20])[C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH:13]=[CH:12][CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[C:21]([OH:23])=[O:22].ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)(Cl)Cl>[O:32]1[C@H:12]2[CH2:11][C@H:10]3[C@:15]([CH3:16])([CH2:14][C@@H:13]12)[C@@H:17]1[C@H:7]([C@H:6]2[C@@:2]([CH2:19][C:18]1=[O:20])([CH3:1])[C@@H:3]([C:21]([OH:23])=[O:22])[CH2:4][CH2:5]2)[CH2:8][CH2:9]3

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 227882705alpha-Androst-2-en-11-one 17beta-carboxylic acid

Product 1

HCID 22788254HCID 22788254, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 5α-androst-2-en-11one 17β-carboxylic acid (1.397 g.) and m-chloroperbenzoic acid (850 mg.) in chloroform (20 ml.) was stirred at room temperature for 3.25 hr. and then diluted with chloroform (75 ml.) prior to washing with 10% aqueous sodium bicarbonate and water. The chloroform solution was dried, filtered and evaporated to give a foam (1.04g.) which, after preparative t.l.c. afforded the pure title compound as a foam; [α]D + 69°, (c 0.3).

Workup

  1. washto washing with 10% aqueous sodium bicarbonate and water
  2. dry with materialThe chloroform solution was dried
  3. filtrationfiltered
  4. customevaporated
  5. customto give a foam (1.04g.) which

Sources & evidence

ORD record
ord-eab4cb42023140f1ac5d110dee3d3b59
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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