Pyridine → Methyl cholate

HRID 1081354Notes

Reaction equation

HRID 1081354 reaction equation
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:29])[CH2:14][CH2:15][C@@H:16]3[C@@:21]4([CH3:27])[CH2:22][CH2:23][C@@H:24]([OH:26])[CH2:25][C@H:20]4[CH2:19][C@@H:18]([OH:28])[C@H:17]3[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].N1C=CC=CC=1.CN(C1C=CC=CN=1)C.CS(Cl)(=O)=[O:47]>ClCCl>[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:29])[C@@H:14]([OH:47])[CH2:15][C@@H:16]3[C@@:21]4([CH3:27])[CH2:22][CH2:23][C@@H:24]([OH:26])[CH2:25][C@H:20]4[CH2:19][C@@H:18]([OH:28])[C@H:17]3[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 1049PyridineHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 11069533Methyl chenodeoxycholate

Product 1

HCID 10960835Methyl cholate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl chenodeoxycholate (27 g, 61.5 mmol) is dissolved in 100 mL dichloromethane (DCM), pyridine (20 mL). Dimethylaminopyridine (DMAP) (1.22 g, 10 mmol) is then added. The reaction mixture is chilled to 0° C., and methanesul-fonyl chloride (7.5 mL, 11.0 g, 96.7 mmol) is added dropwise. The reaction mixture is heated at 60° C. for 3 h, cooled to r.t., washed with 5% HCl, water, sodium bicarbonate, brine, and dried over sodium sulfate. The solvent is evaporated under reduced pressure (1 mm Hg, 80° C. in a bath) to give mesylate 1 as a thick oil, weight 27 g (90%). This material is used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture is heated at 60° C. for 3 h
  2. temperaturecooled to r.t.
  3. washwashed with 5% HCl, water, sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is evaporated under reduced pressure (1 mm Hg, 80° C. in a bath)

Sources & evidence

ORD record
ord-6a0ca3e3ec6141a3846f859025f2ffff
Source dataset
uspto-grants-1996_12
Patent number
US05585470

Reaction notes

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