Tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylpiperidine-1-carboxylate → Tert-butyl 4-acetyl-3-methylpiperidine-1-carboxylate

HRID 1806098Notes

Reaction equation

HRID 1806098 reaction equation
[CH3:1][Mg]Cl.CON(C)[C:7]([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][CH:10]1[CH3:22])=[O:8]>C1COCC1>[C:7]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:11][CH:10]1[CH3:22])(=[O:8])[CH3:1]

Participants

4

Reactant 2

HCID 86601647Tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylpiperidine-1-carboxylateHCID 178418332HCID 178418332, compound

Product 1

HCID 57741702Tert-butyl 4-acetyl-3-methylpiperidine-1-carboxylateYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.0 M methylmagnesium chloride in THF (4.50 mL, 13.5 mmol) was added dropwise to a solution of tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylpiperidine-1-carboxylate (3.10 g, 10.8 mmol) in THF (50 mL) at 0° C. The reaction was warmed to ambient temperature and stirred for 90 minutes. The reaction was partitioned between ether and 2N HCl, washed the organic layer twice with water, brine, dried, and concentrated to afford the title compound (2.32 g, 84.3% yield) as clear oil.

Workup

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

Sources & evidence

ORD record
ord-6c944e9fc6c04bfd9de74a4c8f42004e
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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