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

HRID 1809583Notes

Reaction equation

HRID 1809583 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-0411af851ca542a08fb991a21b08381c
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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