Water → Benzyl 2-oxopiperidine-1-carboxylate

HRID 1972919Notes

Reaction equation

HRID 1972919 reaction equation
C([Li])CCC.[NH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].O>C1COCC1>[O:12]=[C:7]1[CH2:8][CH2:9][CH2:10][CH2:11][N:6]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 126652-PiperidoneHCID 178418339Butyllithium

Product 1

HCID 11096497Benzyl 2-oxopiperidine-1-carboxylateYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (2.5 M in hexanes; 12.11 mL, 30.26 mmol) was added dropwise to a cooled (−78° C.) solution of piperidin-2-one (2.50 g, 25.22 mmol) in THF (100 mL). The mixture was stirred at −78° C. for 2.5 h. A solution of benzyl chloroformate (7.20 mL, 50.44 mmol) in THF (30 mL) was added dropwise. The mixture was stirred at −78 PC for 2 h and then was allowed to warm to rt. Water was added (200 and the mixture was extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried (Na2SO4), and concentrated to dryness to afford 4.13 g (70%) of the desired product. ES-MS m/z 233.91 [M+H]+, HPLC RT (min) 2.76.

Workup

  1. stirringThe mixture was stirred at −78 PC for 2 h
  2. temperatureto warm to rt
  3. extractionthe mixture was extracted with EtOAc (3×100 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5021bfc470a3433e86a99908d37b5465
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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