1-Boc-4-[(N-methoxy-N-methylcarbamoyl)methyl]piperidine → Tert-butyl 4-(2-oxopropyl)piperidine-1-carboxylate

HRID 335257Notes

Reaction equation

HRID 335257 reaction equation
[CH3:1][Mg]Cl.CON(C)[C:7](=[O:22])[CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1>C1COCC1>[O:22]=[C:7]([CH3:1])[CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 229287811-Boc-4-[(N-methoxy-N-methylcarbamoyl)methyl]piperidineHCID 178418332HCID 178418332, compound

Product 1

HCID 12017169Tert-butyl 4-(2-oxopropyl)piperidine-1-carboxylateYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Added dropwise 3.0 M methylmagnesium chloride in THF (8.63 mL, 25.9 mmol) to a solution of tert-butyl 4-(2-(methoxy(methyl)amino)-2-oxoethyl)piperidine-1-carboxylate (5.93 g, 20.7 mmol) in THF (100 mL) at 0° C. Warmed to ambient temperature and stirred for 90 minutes. Partitioned between ether and 2N HCl, washed the organic layer twice with water, brine, dried, and concentrated to afford the title compound (4.95 g, 99.1% yield) as a clear oil.

Workup

  1. customPartitioned between ether and 2N HCl
  2. washwashed the organic layer twice with water, brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-58e7c07da2244c68a3695f2048a78bbe
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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