Methanol → 3alpha-Hydroxy-2beta-methoxy-17beta-methoxycarbonyl-5alpha-androstan-11-one

HRID 267613Notes

Reaction equation

HRID 267613 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:18]([CH3:20])([CH2:19][C@@H:2]12)[C@@H:17]1[C@H:8]([C@H:9]2[C@@:13]([CH2:15][C:16]1=[O:21])([CH3:14])[C@@H:12]([C:22]([O:24][CH3:25])=[O:23])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.[CH3:26][OH:27].S(=O)(=O)(O)O>O>[OH:1][C@@H:3]1[C@@H:2]([O:27][CH3:26])[CH2:19][C@@:18]2([CH3:20])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[C:16](=[O:21])[CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:22]([O:24][CH3:25])=[O:23])[CH2:4]1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 86733131HCID 86733131, compound

Product 1

HCID 227882403alpha-Hydroxy-2beta-methoxy-17beta-methoxycarbonyl-5alpha-androstan-11-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2α,3α-Epoxy-17β-methoxycarbonyl-5α-androstan-11-one (500 mg.) in warm dry methanol (30 ml.) was treated with concentrated sulphuric acid (0.15 ml.). After 30 minutes the solution was poured into stirred water. The precipitated product was isolated, washed with water and dried over sodium hydroxide in vacuo to give fairly pure title compound (420 mg.) as a white powder; m.p. 170°-182°; [α]D + 68°,

Workup

  1. additionAfter 30 minutes the solution was poured
  2. customThe precipitated product was isolated
  3. washwashed with water
  4. dry with materialdried over sodium hydroxide in vacuo

Sources & evidence

ORD record
ord-bb55f724df6f4344aa9065853756c0c4
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

Loading…