Diazomethane → 3alpha-Hydroxy-17beta-methoxycarbonyl-5alpha-androstan-11-one

HRID 267609Notes

Reaction equation

HRID 267609 reaction equation
[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:22]([OH:24])=[O:23])[CH2:3]1.[N+](=[CH2:27])=[N-]>CO.CCOCC>[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:22]([O:24][CH3:27])=[O:23])[CH2:3]1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 227882653alpha-Hydroxy-5alpha-androstan-11-one 17beta-carboxylic acid

Product 1

HCID 705861023alpha-Hydroxy-17beta-methoxycarbonyl-5alpha-androstan-11-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3α-hydroxy-11-oxo-5α-androstane-17β-carboxylic acid (350 mg.) in methanol (20 ml.) and ether (10 ml.) was treated with a dry ethereal solution of diazomethane. After 10 minutes, any unreacted diazomethane was destroyed by the addition of a drop of glacial acetic acid and the mixture was evaporated to small bulk. This was taken up in ether and washed with dilute sodium hydrogen carbonate solution, with water, dried and evaporated to a foam. The product was crystallised from acetone and petrol to give title compound (28/ mg.) as off white needles; m.p. 162 163°; [α]D + 77°.

Workup

  1. customany unreacted diazomethane was destroyed by the addition of a drop of glacial acetic acid
  2. customthe mixture was evaporated to small bulk
  3. washwashed with dilute sodium hydrogen carbonate solution, with water
  4. customdried
  5. customevaporated to a foam
  6. customThe product was crystallised from acetone and petrol

Sources & evidence

ORD record
ord-78fd05cd098e49a798bd68922823d261
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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