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

HRID 1527123Notes

Reaction equation

HRID 1527123 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 16 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-004baddd04b54981b3ab348dba02d8d3
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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