Imidazole → (3R)-1-Benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidine

HRID 546464Notes

Reaction equation

HRID 546464 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:19](Cl)([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinol

Product 1

HCID 57432600(3R)-1-Benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3R)-1-Benzyl-3-hydroxypyrrolidine (500 μl) and imidazole (466 mg) were dissolved in N,N-dimethyl-formamide (15 ml), tert-butyldiphenylsilyl chloride (1.57 ml) was added under ice cooling, and the mixture was stirred at room temperature for 9 days. After the solvent was distilled off under reduced pressure, and dichloromethane and water were added to the residue to conduct liquid separation, the resultant organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to flash column chromatography on silica gel (hexane:ethyl acetate=3:1) to obtain the title compound (1.27 g) as a yellow oil.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure, and dichloromethane and water
  2. additionwere added to the residue
  3. customliquid separation
  4. dry with materialthe resultant organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c4173581dadc41ac893ba21533839a03
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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