Imidazole → HCID 57501821, compound

HRID 1245026Notes

Reaction equation

HRID 1245026 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH:14][C@H:15]1[CH2:23][N:22]2[C@H:17]([CH2:18][C:19](=[O:24])[CH2:20][CH2:21]2)[CH2:16]1.O>ClCCl>[Si:6]([O:14][C@H:15]1[CH2:23][N:22]2[C@H:17]([CH2:18][C:19](=[O:24])[CH2:20][CH2:21]2)[CH2:16]1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 45083132HCID 45083132, compound

Product 1

HCID 57501821HCID 57501821, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.70 g (24.9 mmol) of imidazole and 1.88 g (12.5 mmol) of t-butyldimethylsilyl chloride were added to a solution of 1.30 g (8.1 mmol) of (2R,8aS)-2-hydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-7-one [obtained as described in Preparative Example 2(i)′ above] in 30 ml of dichloromethane and the resulting mixture was stirred for 20 hours at room temperature. At the end of this time, water was added and the reaction mixture was extracted with dichloromethane. The organic extract was washed with water and concentrated by evaporation under reduced pressure, and the resulting residue was then purified by chromatography on an alumina column using a 9:1 by volume mixture of hexane and ethyl acetate as the elaunt to afford 1.98 g (yield: 88%) of the title compound as a colorless oil.

Workup

  1. customobtained
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customthe resulting residue was then purified by chromatography on an alumina column
  7. additionby volume mixture of hexane and ethyl acetate as the elaunt

Sources & evidence

ORD record
ord-e76ce5f25c3c4071b6f1a8b3332b5936
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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