Imidazole → HCID 59710103, compound

HRID 2221010Notes

Reaction equation

HRID 2221010 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:3]1[C:14]([O:16][CH2:17][CH3:18])=[O:15].N1C=CN=C1.Cl[Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>O.Cl.CN(C1C=CC=CN=1)C>[CH3:29][C:28]([Si:25]([CH3:27])([CH3:26])[O:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:3]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])([CH3:31])[CH3:30]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 59710385HCID 59710385, compound

Product 1

HCID 59710103HCID 59710103, compoundYield 88.4%

Reagents, catalysts & solvents 3

HCID 218852-DimethylaminopyridineCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

1-(1,1-dimethylethyl) 2-ethyl(2S,3S)-3-hydroxy-1,2-pyrrolidinedicarboxylate (8.98 g, 34.7 mmol), imidazole (2.36 g, 34.7 mmol), dimethylaminopyridine (50 mg, catalytic) and chloro(1,1-dimethylethyl)dimethylsilane (4.96 g, 32.9 mmol) were stirred at room temperature for 16 hours. The reaction was diluted with water and 1N HCl to make the mixture acidic. The mixture was extracted three times with methylene chloride. The organic layer was washed with 1M HCl, dried over MgSO4 to give the title compound as a clear brown oil (10.88 g, 29.1 mmol). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.0 (m, 6 H) 0.8 (m, 9 H) 1.2 (m, 3 H) 1.3 (m, 9 H) 1.7 (m, 1 H) 1.9 (m, 1 H) 3.4 (m, 2 H) 3.9 (m, 1 H) 4.1 (m, 2 H) 4.4 (m, 1 H). ES+=374.30.

Workup

  1. extractionThe mixture was extracted three times with methylene chloride
  2. washThe organic layer was washed with 1M HCl
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-e4ceb892cbf844a2b723d1b269a6fa1d
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

Loading…