Dimethylformamide → 1-Benzyl-2-(tert-butyldimethylsilyloxymethyl)piperidine

HRID 893282Notes

Reaction equation

HRID 893282 reaction equation
CN(C=O)C.[H-].[Na+].[Si:8]([O:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][NH:18]1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[CH2:23]([N:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[CH2:16][O:15][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 121857462-{[(Tert-butyldimethylsilyl)oxy]methyl}piperidine

Product 1

HCID 198919761-Benzyl-2-(tert-butyldimethylsilyloxymethyl)piperidineYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a DMF (4 ml) solution of 60% sodium hydride (0.21 g, 5.2 mmol) was dropwise added a DMF (4 ml) solution of 2-(tert-butyldimethylsilyloxymethyl)piperidine (1.00 g, 4.4 mmol) at room temperature. The mixture was stirred at room temperature for 30 min., to which was then dropwise added a THF (1 ml) solution of benzyl bromide (0.75 g, 4.4 mmol). After stirring at room temperature for additional 30 min., a reaction solution was poured onto water followed by extraction with diethyl ether (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 give 1.30 g of the title compound.

Workup

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

Sources & evidence

ORD record
ord-ae2483378bdc49e099e39fbbf8695e97
Source dataset
uspto-grants-1992_06
Patent number
US05124324

Reaction notes

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