Hydrochloric Acid → 4-Acetyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 2206642Notes

Reaction equation

HRID 2206642 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].[CH3:20][Mg]Br.Cl>O1CCCC1>[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])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 109879834-Acetyl-piperidine-1-carboxylic acid tert-butyl esterYield 77.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (4.0 g, 14.69 mmol) in tetrahydrofuran (50 mL) was added methylmagnesium bromide solution (5.25 g, 44.06 mmol, 3M) at −70° C. over 0.5 hour. The resultant mixture was stirred at room temperature for 6 hours. The reaction solution was adjusted pH to 6.0 by 1.0M hydrochloride solution. The aqueous phase was extracted with ethyl acetate (100 ml*3). The combined organic layers was washed with brine, dried over sodium sulfate and concentrated under vacuum to give tert-butyl 4-acetylpiperidine-1-carboxylate as a yellow liquid (2.6 g, yield 77.8%). LRMS (M+H+) m/z: calcd 227.15. found 228.

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate (100 ml*3)
  2. washThe combined organic layers was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f6ca7a768e744d528bfdcfbd1802539d
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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