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

HRID 2104351Notes

Reaction equation

HRID 2104351 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-dimethylformamide (15 mL), and tert-butyldiphenylsilyl chloride (1.57 mL) was added to the solution under ice cooling, followed by stirring at room temperature for 9 days. The solvent was distilled away under reduced pressure, and the residue was partitioned by adding methylene chloride and water. The organic layer was dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure. The residue was subjected to silica gel flash column chromatography (hexane ethyl acetate=3:1), to thereby give the title compound (1.27 g).

Workup

  1. distillationThe solvent was distilled away under reduced pressure
  2. customthe residue was partitioned
  3. additionby adding methylene chloride and water
  4. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  5. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-7e537c32ef5944c08399ddf37372dacb
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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