Imidazole → HCID 178460990, compound

HRID 1160256Notes

Reaction equation

HRID 1160256 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.N1C=CN=C1.[CH:36]([Si:39](Cl)([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41])([CH3:38])[CH3:37]>CN(C=O)C>[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:39]([CH:43]([CH3:45])[CH3:44])([CH:40]([CH3:42])[CH3:41])[CH:36]([CH3:38])[CH3:37])[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

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 178516684HCID 178516684, compound

Product 1

HCID 178460990HCID 178460990, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Mix (R)-3-(4-Benzyloxy-2,6-dichloro-benzyl)-trans-1-(4-hydroxy-cyclohexyl)-pyrrolidin-2-one (Preparation 16) (1.37 g, 3.07 mmol) and imidazole (0.527 g, 68.08 mmol) in 10 ml of dry DMF. Add triisopropylsilylchloride (0.81 ml, 3.07 mmol) dropwise and stir at room temperature for 5 hours. Quench with 1N HCl and extract with ethyl acetate. Wash the extract with NaHCO3 and brine. Dry over magnesium sulfate, filter, and concentrate. After flash column chromatography, receive 1.83 g (99%) of the title compound: Mass spectrum (apci) m/z=604 (M+H).

Workup

  1. customQuench with 1N HCl
  2. extractionextract with ethyl acetate
  3. washWash the
  4. extractionextract with NaHCO3 and brine
  5. dry with materialDry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-ea9a2a6f0395484bade7c9013fd2acd0
Source dataset
uspto-grants-2010_10
Patent number
US07816349B2

Reaction notes

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