Boron trifluoride etherate → Methyl cholate

HRID 1779843Notes

Reaction equation

HRID 1779843 reaction equation
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:29])[C@@H:13]([OH:28])[CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23]([OH:25])[CH2:24][C@H:19]4[CH2:18][C@@H:17]([OH:27])[C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].B(F)(F)F.[CH3:34]COCC>CO>[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:29])[C@@H:13]([OH:28])[CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23]([OH:25])[CH2:24][C@H:19]4[CH2:18][C@@H:17]([OH:27])[C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([O:7][CH3:34])=[O:6]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 221493Cholic Acid

Product 1

HCID 10960835Methyl cholateYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of cholic acid (300 g, 0.73 mol) in 1.1 L methanol is added boron trifloride etherate. The mixture is refluxed for 1 h. After cooling, a solid precipitate 2 is collected by filtration. The mother liquor is kept in a refrigerator to give another crop of product The combined product (295 g, 95%) is dried under vacuum and used for the next reaction without further purification.

Workup

  1. temperatureThe mixture is refluxed for 1 h
  2. temperatureAfter cooling
  3. filtrationa solid precipitate 2 is collected by filtration

Sources & evidence

ORD record
ord-8142d0dd128747ebb9c9ffb03de3414d
Source dataset
uspto-grants-1997_05
Patent number
US05627270

Reaction notes

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