Hydrogen Bromide → 2beta-Bromo-17beta-cyano-3alpha-hydroxy-5alpha-androstan-11-one

HRID 267621Notes

Reaction equation

HRID 267621 reaction equation
[BrH:1].[C:2]([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][C@@H:15]2[O:24][C@@H:16]2[CH2:17]1)[CH2:12][CH2:11]3)#[N:3]>C(Cl)(Cl)Cl>[Br:1][C@H:16]1[CH2:17][C@@:18]2([CH3:19])[C@@H:13]([CH2:12][CH2:11][C@@H:10]3[C@@H:20]2[C:21](=[O:23])[CH2:22][C@@:5]2([CH3:6])[C@H:7]3[CH2:8][CH2:9][C@@H:4]2[C:2]#[N:3])[CH2:14][C@@H:15]1[OH:24]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 8673313717beta-Cyano-2alpha,3alpha-epoxy-5alpha-androstan-11-one

Product 1

HCID 867331362beta-Bromo-17beta-cyano-3alpha-hydroxy-5alpha-androstan-11-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Aqueous 48% hydrobromic acid (60 ml.) was added to a solution of 17β-cyano-2α,3α-epoxy-5α-androstan-11-one (3.03g.) in chloroform (175ml.) and the mixture stirred at room temperature for 1 hr. The organic phase was separated, washed with aqueous 10% sodium bicarbonate and water and dried. Filtration and evaporation followed by preparative t.l.c. afforded the pure title compound as a white froth (2.16g.); [α]D + 68.5°, (c 0.6).

Workup

  1. customThe organic phase was separated
  2. washwashed with aqueous 10% sodium bicarbonate and water
  3. customdried
  4. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-1649bf722b3c427887c307b0423678c0
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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