m-Chloroperbenzoic acid → 17beta-Cyano-2alpha,3alpha-epoxy-5alpha-androstan-11-one

HRID 267638Notes

Reaction equation

HRID 267638 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([C:20](=[O:22])[CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C@H:12]([CH2:13][CH:14]=[CH:15][CH2:16]1)[CH2:11][CH2:10]3)#[N:2].ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl>[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([C:20](=[O:22])[CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C@H:12]([CH2:13][C@@H:14]2[O:31][C@@H:15]2[CH2:16]1)[CH2:11][CH2:10]3)#[N:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 8673314517beta-Cyano-5alpha-androst-2-en-11-one

Product 1

HCID 8673313717beta-Cyano-2alpha,3alpha-epoxy-5alpha-androstan-11-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 17β-cyano-5α-androst-2-en-11-one (2.8g.) and 85% m-chloroperbenzoic acid (2.0g.) in chloroform (50 ml.) was stirred for 1.5 hour at room temperature and then diluted with chloroform (75 ml.). This solution was washed with aqueous 10% sodium bicarbonate and water prior to drying. Filtration and evaporation afforded a solid (3.18g.) which was recrystallised from ether/petrol to afford the pure title compound; m.p. 206°-208°; [α]D + 93°, (c 0.7).

Workup

  1. washThis solution was washed with aqueous 10% sodium bicarbonate and water
  2. customto drying
  3. filtrationFiltration and evaporation
  4. customafforded a solid (3.18g.) which
  5. customwas recrystallised from ether/petrol

Sources & evidence

ORD record
ord-ff1601e1bbdb440faa7fdc546d11b121
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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