Imidazole → HCID 67264813, compound

HRID 1041253Notes

Reaction equation

HRID 1041253 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]1[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14]1)(=[O:12])=[O:11])([O-:3])=[O:2].[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].N1C=CN=C1>CN(C)C=O>[C:22]([Si:19]([CH3:21])([CH3:20])[O:18][CH:15]1[CH2:16][CH2:17][N:13]([S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:11])=[O:12])[CH2:14]1)([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 62918137HCID 62918137, compound

Product 1

HCID 67264813HCID 67264813, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-Nitro-benzenesulfonyl)-pyrrolidin-3-ol (12.25 g, 0.04499 mol) in N,N-dimethylformamide (40 mL) was treated with tert-butyldimethylsilyl chloride (8.137 g, 0.05399 mol) and 1H-imidazole (4.594 g, 0.06748 mol) at room temperature for 3 h. The reaction mixture was partitioned between water and ethyl ether, and the layers were separated. The aqueous layer was extracted twice with ethyl ether, and then the organic extracts were washed extensively with water, then once with brine, dried (MgSO4), filtered and concentrated to give 3-(tert-butyl-dimethyl-silanyloxy)-1-(2-nitro-benzenesulfonyl)-pyrrolidine as an off-white solid (17.4 g, 92%).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl ether
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted twice with ethyl ether
  4. washthe organic extracts were washed extensively with water
  5. dry with materialonce with brine, dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-233673356ff148238df27142453735df
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…