Hydrochloric Acid → 17beta-Methoxycarbonyl-5alpha-androst-2-en-11-one

HRID 267630Notes

Reaction equation

HRID 267630 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([C:22](=[O:24])[CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C@H:14]([CH2:15][C@@H:16](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)=[O:4].Cl>N1C(C)=CC(C)=CC=1C>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([C:22](=[O:24])[CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C@H:14]([CH2:15][CH:16]=[CH:17][CH2:18]1)[CH2:13][CH2:12]3)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86733143HCID 86733143, compound

Product 1

HCID 2278825117beta-Methoxycarbonyl-5alpha-androst-2-en-11-oneYield 51.2%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

A solution of 17β-methoxycarbonyl-3β-toluene-p-sulphonyloxy-5α-androstan-11-one (1.01g.) in hot collidine (5 ml.) was refluxed for 30 minutes. The solution was cooled and poured into diluted hydrochloric acid and ice, and stirred. The product was filtered, washed with water, dried and purified by filtering it through a column of alumina, eluting with ether. The eluate was evaporated to a residue and crystallisation from ether and hexane gave title compound (340 mg.) as colourless rods; m.p. 169°-175°; [α]D + 139°.

Workup

  1. temperatureThe solution was cooled
  2. filtrationThe product was filtered
  3. washwashed with water
  4. customdried
  5. custompurified
  6. filtrationby filtering it through a column of alumina
  7. washeluting with ether
  8. customThe eluate was evaporated to a residue and crystallisation from ether and hexane

Sources & evidence

ORD record
ord-adfd62dbdd12400fb3ddd3395d3ba9e0
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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