17beta-Carbamoyl-5alpha-androst-2-en-11-one → 17beta-Cyano-5alpha-androst-2-en-11-one

HRID 267637Notes

Reaction equation

HRID 267637 reaction equation
[C:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:20]([C:21](=[O:23])[CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C@H:13]([CH2:14][CH:15]=[CH:16][CH2:17]1)[CH2:12][CH2:11]3)(=O)[NH2:2]>C(Cl)(Cl)Cl>[C:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:20]([C:21](=[O:23])[CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C@H:13]([CH2:14][CH:15]=[CH:16][CH2:17]1)[CH2:12][CH2:11]3)#[N:2]

Participants

3

Reactant 1

HCID 8673314617beta-Carbamoyl-5alpha-androst-2-en-11-one

Product 1

HCID 8673314517beta-Cyano-5alpha-androst-2-en-11-oneYield 56.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

17β-Carbamoyl-5α-androst-2-en-11-one (4.0g., 13 mmole) and polyphosphate ester (20g.) were refluxed in chloroform (200 ml.) for 20 hr. The chloroform was removed by evaporation and the residue stirred with aqueous 10% sodium carbonate (150 ml.) for an hour. The mixture was extracted with ether and the extract washed (H2O), dried filtered and evaporated to give a solid which, after recrystallisation from chloroform/cyclohexane, gave the title compound (2.17g); m.p. 189°-191°; [α]D + 152°, (c 0.9).

Workup

  1. customThe chloroform was removed by evaporation
  2. extractionThe mixture was extracted with ether
  3. washthe extract washed (H2O)
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give a solid which
  8. customafter recrystallisation from chloroform/cyclohexane

Sources & evidence

ORD record
ord-038dff8679e547fc81cedbb1e9756d27
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

Loading…