Potassium Hydroxide → HCID 18647598, compound

HRID 1682178Notes

Reaction equation

HRID 1682178 reaction equation
[OH:1][C@@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:4]([C@@H:5]([F:30])[C:6](=[O:29])[C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][C:15]([O:17]C)=[O:16])[CH2:3]1.[OH-].[K+]>CO>[OH:1][C@@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:4]([C@@H:5]([F:30])[C:6](=[O:29])[C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18647601HCID 18647601, compound

Product 1

HCID 18647598HCID 18647598, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of methyl 3α-hydroxy-6α-fluoro-7-keto-5β-cholanoate (0.6 g, 1.42 mmoles) in methanol (46 ml) was added to a methanol solution of 10% potassium hydroxide (82 ml) and the resulting solution was kept under magnetic stirring overnight. Then methanol was removed under vacuum, the residue was taken up into water (50 ml), acidified with 10% hydrochloric acid and extracted with methylene chloride (3×30 ml). The combined organic phases were washed with brine (1×20 ml) and dried over sodium sulfate. After evaporation of the solvent, the residue (0.62 g) was subjected to flash chromatography on silica, eluting with methylene chloride/methanol 95:5, to obtain 0.55 g of a pure product (95%).

Workup

  1. customThen methanol was removed under vacuum
  2. extractionextracted with methylene chloride (3×30 ml)
  3. washThe combined organic phases were washed with brine (1×20 ml)
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent
  6. washeluting with methylene chloride/methanol 95:5

Sources & evidence

ORD record
ord-cb32a63c3cb2405dae49fee31078f33f
Source dataset
uspto-grants-1992_12
Patent number
US05175320

Reaction notes

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