Benzyl 2-methyl-4-oxopiperidine-1-carboxylate → Benzyl (2S)-2-methyl-4-oxopiperidine-1-carboxylate

HRID 1510147Notes

Reaction equation

HRID 1510147 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[CH2:5][CH2:4][N:3]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]>CO>[CH3:1][C@H:2]1[CH2:7][C:6](=[O:8])[CH2:5][CH2:4][N:3]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

3

Reactant 1

HCID 46941997Benzyl 2-methyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 57475593Benzyl (2S)-2-methyl-4-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude Racemic benzyl 2-methyl-4-oxopiperidine-1-carboxylate was dissolved in MeOH and chromatographed on a 10 cm Chiralpak AD column eluting with 100% MeOH in 2.5 g injections to give the two separated enantiomers. The desired enantiomer eluted first, 95% ee.

Workup

  1. customchromatographed on a 10 cm Chiralpak AD column
  2. washeluting with 100% MeOH in 2.5 g injections
  3. customto give the two separated enantiomers
  4. washThe desired enantiomer eluted first

Sources & evidence

ORD record
ord-b930b4c6992d4d1d90b8a4e5ea707c32
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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