Imidazole → 2-{[(Tert-butyldimethylsilyl)oxy]methyl}piperidine

HRID 893281Notes

Reaction equation

HRID 893281 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8].N1C=CN=C1.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15]>CN(C=O)C>[Si:18]([O:8][CH2:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][NH:1]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 94263Piperidin-2-ylmethanol

Product 1

HCID 121857462-{[(Tert-butyldimethylsilyl)oxy]methyl}piperidineYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (3 ml) solution of 2-piperidinemethanol (1.00 g, 8.7 mmol) and imidazole (1.48 g, 21.7 mmol) was added tert-butyldimethylchlorosilane (1.57 g, 10.4 mmol) at room temperature. After stirring for 30 min., a reaction solution was poured onto water followed by extraction with diethyl ether (about 30 ml). The extract was washed successively with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to afford 1.61 g of the title compound.

Workup

  1. additiona reaction solution was poured onto water
  2. extractionfollowed by extraction with diethyl ether (about 30 ml)
  3. washThe extract was washed successively with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-53ee4661186c4a52b49464a6a0306cf2
Source dataset
uspto-grants-1992_06
Patent number
US05124324

Reaction notes

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