Water → 1-Tert-butyl 4-ethyl 4-(methoxymethyl)piperidine-1,4-dicarboxylate

HRID 1910403Notes

Reaction equation

HRID 1910403 reaction equation
[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:29][O:30][CH2:31]Cl.O>C1COCC1.C1(C)C=CC=CC=1>[CH3:29][O:30][CH2:31][C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2][N:1]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylateHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 667414481-Tert-butyl 4-ethyl 4-(methoxymethyl)piperidine-1,4-dicarboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (2.57 g) in THF (26 ml) was added 0.5 M solution of potassium bis(trimethylsilyl)amide in toluene (24.0 ml) under at −70° C. After 15 minutes, chloromethyl methyl ether (1.2 ml) was added and it was stirred at 0° C. for 2 hours. Water was added and extracted with EtOAc. The organic phase was washed with water and brine, dried over MgSO4, evaporated under reduced pressure. The residue was purified by silica gel column to give 1-tert-butyl 4-ethyl 4-(methoxymethyl)piperidine-1,4-dicarboxylate (2.05 g) as oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-178cb128f3254778b6e57fe4ce619446
Source dataset
uspto-grants-2013_12
Patent number
US08603975B2

Reaction notes

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