Water → HCID 12796517, compound

HRID 2049490Notes

Reaction equation

HRID 2049490 reaction equation
Br[C@@H:2]1[C@@H:7]([OH:8])[CH2:6][C@H:5]2[C@H:9]3[C@H:19]([C@H:20]([N:22]([CH3:24])[CH3:23])[CH2:21][C@:3]12[CH3:4])[C@:17]1([CH3:18])[C@H:12]([CH2:13][C@H:14]([OH:28])[C@@H:15]([O:25][CH2:26][CH3:27])[CH2:16]1)[CH2:11][CH2:10]3.O.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:24][N:22]([C@@H:20]1[CH2:21][C@@:3]2([CH3:4])[C@@H:5]([CH2:6][C@@H:7]3[O:8][C@@H:2]32)[C@H:9]2[C@H:19]1[C@:17]1([CH3:18])[C@@H:12]([CH2:11][CH2:10]2)[CH2:13][C@H:14]([OH:28])[C@@H:15]([O:25][CH2:26][CH3:27])[CH2:16]1)[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 12796519HCID 12796519, compound

Product 1

HCID 12796517HCID 12796517, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 17α-bromo-11α-N,N-dimethylamino-2β-ethoxy-5α-androstane-3α,16β-diol (212 mg) in methanol (33 ml) containing water (1.2 ml) was treated with a 40% solution of potassium carbonate (0.66 ml) and the mixture was refluxed. After 1 hour most of the solvent was evaporated and the residue was partitioned between ethyl acetate and water. The washed and dried (Na2SO4) organic layer was evaporated and the residue was purified by preparative thin layer chromatography over silica (ethyl acetate--petroleum ether 1:1) and crystallization from aqueous methanol to give the title compound (80 mg) m.p. 149°-151°, [α]D +6.7°.

Workup

  1. temperaturethe mixture was refluxed
  2. customAfter 1 hour most of the solvent was evaporated
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe washed
  5. dry with materialdried (Na2SO4) organic layer
  6. customwas evaporated
  7. customthe residue was purified by preparative thin layer chromatography over silica (ethyl acetate--petroleum ether 1:1) and crystallization from aqueous methanol

Sources & evidence

ORD record
ord-b124dc3d24f044929e92b3382d40405e
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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