Water → Tert-butyl 4-methoxypiperidine-1-carboxylate

HRID 2213007Notes

Reaction equation

HRID 2213007 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[CH3:17]I.O>CN(C)C=O>[CH3:17][O:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 21955381Tert-butyl 4-methoxypiperidine-1-carboxylateYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 2.98 g, 74.5 mmol) was added to a solution of 1,1-dimethylethyl 4-hydroxy-1-piperidinecarboxylate (5.0 g, 24.8 mmol) in dimethylformamide (30 mL) and the mixture was stirred for 5 minutes. Methyl iodide (4.64 mL, 74.5 mmol) was added and the mixture was stirred for 30 minutes. Water (50 mL) was added and the mixture was extracted with diethyl ether (2×50 mL). The combined organic fractions were washed with water (4×50 mL) and brine, dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound (5.3 g, 99%). m/z (ES+) 216 (M+1).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionthe mixture was extracted with diethyl ether (2×50 mL)
  3. washThe combined organic fractions were washed with water (4×50 mL) and brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7c7e393b896b488b8fd1a16f383a3ad4
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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