Imidazole → 1-(Benzyloxycarbonyl)-3-(tert-butyldimethylsilyloxymethyl)piperidine

HRID 602123Notes

Reaction equation

HRID 602123 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH2:27][CH:26]([CH2:30][OH:31])[CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH2:27][CH:26]([CH2:30][O:31][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])[CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 2776577Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 589926311-(Benzyloxycarbonyl)-3-(tert-butyldimethylsilyloxymethyl)piperidineYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (3.00 g, 44.0 mmol) and tert-butyldimethylsilyl chloride (6.63 g, 44.0 mmol) were added to 1-(benzyloxycarbonyl)piperidin-3-yl methanol (9.15 g, 36.7 mmol) in N,N-dimethylformamide (40 mL). The solution was stirred at room temperature for 6 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract washed with brine and was dried over magnesium sulfate, followed by evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 13.2 g (99%) of the desired compound as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract washed with brine
  3. dry with materialwas dried over magnesium sulfate
  4. customfollowed by evaporation of the solvent
  5. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1)

Sources & evidence

ORD record
ord-cb168814464c40849f6e4caa3ca11a9f
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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