tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate → Tert-butyl 4-benzoylpiperidine-1-carboxylate

HRID 2382191Notes

Reaction equation

HRID 2382191 reaction equation
CON(C)[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5].[C:20]1([Mg]Cl)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[C:4]([CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]1)(=[O:5])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylateHCID 178478979HCID 178478979, compound

Product 1

HCID 10827307Tert-butyl 4-benzoylpiperidine-1-carboxylateYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (8.0 g, 29.4 mmol) in THF (25 mL) was added PhMgCl (8.0 g, 58.8 mmol) dropwise at 0° C. After stirring at rt for 2 h, the reaction was quenched with ammonium chloride solution and extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated under vacuum to afford tert-butyl 4-benzoylpiperidine-1-carboxylate (5 g, 59% yield) as a pale yellow solid which was used directly in the next step.

Workup

  1. customthe reaction was quenched with ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5aa05b7ef335495ab0f1d54e49721986
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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