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

HRID 911850Notes

Reaction equation

HRID 911850 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-7bad11a0963741e9ae27eabfa6631808
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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