Pyridine → 3-(Chloromethoxycarbonyl) Cholesterol

HRID 1406

Reaction equation

HRID 1406 reaction equation
Cl[C:2]([O:4][CH2:5][Cl:6])=[O:3].[CH3:7][CH:8]([CH2:10][CH2:11][CH2:12][C@H:13]([C@@H:15]1[C@:33]2([CH3:34])[C@H:18]([C@H:19]3[C@H:30]([CH2:31][CH2:32]2)[C@:28]2([CH3:29])[C:22]([CH2:23][C@H:24]([CH2:26][CH2:27]2)[OH:25])=[CH:21][CH2:20]3)[CH2:17][CH2:16]1)[CH3:14])[CH3:9].N1C=CC=CC=1>C(Cl)Cl>[Cl:6][CH2:5][O:4][C:2]([C@:24]1([OH:25])[CH2:26][CH2:27][C@@:28]2([CH3:29])[C:22](=[CH:21][CH2:20][C@@H:19]3[C@@H:30]2[CH2:31][CH2:32][C@@:33]2([CH3:34])[C@H:18]3[CH2:17][CH2:16][C@@H:15]2[C@H:13]([CH3:14])[CH2:12][CH2:11][CH2:10][CH:8]([CH3:9])[CH3:7])[CH2:23]1)=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5997CholesterolHCID 62754Chloromethyl chloroformate

Product 1

HCID 571798753-(Chloromethoxycarbonyl) Cholesterol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chloromethyl chloroformate (1.96 g, 15.2 mmol) and cholesterol (5.0 g, 12.9 mmol) was dissolved in CH2Cl2 (10 ml). The solution was cooled. Pyridine (1.21 g, 15.3 mmol) was dripped into the stirred solution over 5 minutes. Heat was produced and the reaction gave a clear solution from a somewhat unclear starting solution. After 24 hours at room temperature, the mixture was diluted with CH2Cl2 (50 ml), washed with 0.5M HCl (50 ml) and water (3×25 ml). After treatment with MgSO4, the solution was evaporated to dryness.

Workup

  1. temperatureThe solution was cooled
  2. temperatureHeat
  3. customwas produced
  4. customthe reaction gave a clear solution from
  5. washwashed with 0.5M HCl (50 ml) and water (3×25 ml)
  6. customAfter treatment with MgSO4, the solution was evaporated to dryness

Sources & evidence

ORD record
ord-169f88b27a294c15b3d94e8de0e682c6
Source dataset
uspto-grants-1998_03
Patent number
US05725840

Linked notes

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