Imidazole → HCID 68160193, compound

HRID 1468761Notes

Reaction equation

HRID 1468761 reaction equation
[C:1]1([C@H:7]([N:9]2[CH2:13][CH2:12][C@H:11]([CH2:14][OH:15])[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CN=C1.[C:21]([Si:25]([CH3:28])([CH3:27])Cl)([CH3:24])([CH3:23])[CH3:22].O>CN(C)C=O>[Si:25]([O:15][CH2:14][C@H:11]1[CH2:12][CH2:13][N:9]([C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH3:8])[CH2:10]1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 13772859{(3S)-1-[(1R)-1-Phenylethyl]pyrrolidin-3-yl}methanol

Product 1

HCID 68160193HCID 68160193, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of {(3S)-1-[(1R)-1-phenylethyl]pyrrolidin-3-yl}methanol (6.62 g, 32 mmol) and imidazole (4.77 g, 70 mmol) in N,N-dimethylformamide (90 ml) was added tert-butyldimethylchlorosilane (5.28 g, 35 mmol) at 0° C. and the resulting mixture was warmed to room temperature. The reaction mixture was stirred overnight and poured into water. Extraction with ethyl acetate was performed. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solution was concentrated and the residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=90/10 to 75/25) to afford (3S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-[(1R)-1-phenylethyl]pyrrolidine (8.81 g, 27.6 mmol, 86%) as a colorless oil.

Workup

  1. extractionExtraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe solution was concentrated
  5. customthe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=90/10 to 75/25)

Sources & evidence

ORD record
ord-d950d0723cea492fab94e665ebfc3dcf
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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