Methanol → HCID 9888298, compound

HRID 566888Notes

Reaction equation

HRID 566888 reaction equation
C([O:9][C@H:10]1[CH2:35][CH2:34][C@@:33]2([CH3:36])[C@@H:12]([CH2:13][CH2:14][C:15]3[C:16]4[C@:29]([CH3:37])([CH2:30][CH2:31][C:32]=32)[C@@H:19]([C@H:20]([CH3:28])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH:17]=4)[C:11]1([CH3:39])[CH3:38])(=O)C1C=CC=CC=1.CO.O>O1CCCC1>[CH3:39][C:11]1([CH3:38])[C@@H:10]([OH:9])[CH2:35][CH2:34][C@@:33]2([CH3:36])[C@H:12]1[CH2:13][CH2:14][C:15]1[C:16]3[C@:29]([CH3:37])([CH2:30][CH2:31][C:32]=12)[C@@H:19]([C@H:20]([CH3:28])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:18][CH:17]=3

Participants

5

Reactant 3

HCID 887MethanolHCID 962Water2×HCID 54233119HCID 54233119, compound

Product 1

HCID 9888298HCID 9888298, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

—Potassium hydroxide (0.45 g) was added to a solution of compound 13 (0.84 g) in a mixture of tetrahydrofuran (8.4 ml), methanol (8.4 ml) and water (0.45 ml). The mixture was heated under reflux overnight. After cooling, water was added and the resulting precipitate collected by filtration. The residue was washed with water and dried. Column chromatography and crystallization from dichloromethane/acetone afforded (3β,5α,20R)-4,4,20-trimethyl-21-phenylpregna-8,14-dien-3-ol (1) (0.29 g). M.p. 179-186° C. The product contained 30% (w/w) of (3β,5α,20R)-4,4,20-trimethyl-21-phenylpregna-6,8(14)-dien-3-ol.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. filtrationthe resulting precipitate collected by filtration
  5. washThe residue was washed with water
  6. customdried
  7. customColumn chromatography and crystallization from dichloromethane/acetone

Sources & evidence

ORD record
ord-ed8f3a024e1048de84998877a3272c68
Source dataset
uspto-grants-2001_01
Patent number
US06177420B1

Reaction notes

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