Imidazole → HCID 178455350, compound

HRID 415987Notes

Reaction equation

HRID 415987 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[C:27]([Cl:29])[C:12]([CH2:13][C@@H:14]2[CH2:18][CH2:17][N:16]([C@H:19]3[CH2:24][CH2:23][C@@H:22]([OH:25])[CH2:21][CH2:20]3)[C:15]2=[O:26])=[C:11]([Cl:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:31](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].N1C=CN=C1>CN(C)C=O.[Cl-].[Na+].O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Cl:30])[C:12]([CH2:13][C@@H:14]2[CH2:18][CH2:17][N:16]([C@H:19]3[CH2:20][CH2:21][C@@H:22]([O:25][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:23][CH2:24]3)[C:15]2=[O:26])=[C:27]([Cl:29])[CH:28]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178516683HCID 178516683, compound

Product 1

HCID 178455350HCID 178455350, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Combine 10.8 g (R)-3-(4-benzyloxy-2,6-dichloro-benzyl)-cis-1-(4-hydroxy-cyclohexyl)-pyrrolidin-2-one, 5.4 g tert-butyldimethylsilylchloride, and 2.7 g imidazole in 50 mL dry dimethylformamide and stir at ambient temperature over night. Pour into 300 mL brine and extract twice with 200 mL diethyl ether. Wash the combined extracts with brine, dry over magnesium sulfate and concentrate to dryness under vacuum. Purify by silica gel chromatography using 10-15% ethyl acetate in hexanes to recover 11.5 g of the product as an oil.

Workup

  1. extractionextract twice with 200 mL diethyl ether
  2. washWash the combined extracts with brine
  3. dry with materialdry over magnesium sulfate
  4. concentrationconcentrate to dryness under vacuum
  5. customPurify by silica gel chromatography
  6. customto recover 11.5 g of the product as an oil

Sources & evidence

ORD record
ord-c468cdf08595455899b7e813c9113ecb
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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