Methyl morpholine oxide → Benzyl 3,3-dimethyl-4-oxopyrrolidine-1-carboxylate

HRID 1366501Notes

Reaction equation

HRID 1366501 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:4][C:3]1([CH3:18])[CH3:17].C[N+]1([O-])CCOCC1>CC#N>[CH3:17][C:3]1([CH3:18])[C:2](=[O:1])[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:4]1

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66936034HCID 66936034, compound

Product 1

HCID 66936222Benzyl 3,3-dimethyl-4-oxopyrrolidine-1-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of phenylmethyl (4R)-4-hydroxy-3,3-dimethyl-1-pyrrolidinecarboxylate (1.4088 g, 5.651 mmol) in MeCN (50 mL) was added N-methylmorpholine-N-oxide (0.861 g, 7.350 mmol) and tetra-N-propylammonium perruthenate (0.099 g, 0.282 mmol). The solution was stirred for 90 min, concentrated in vacuo, and purified directly by silica gel chromatography (20% EtOAc in hexanes) to give phenylmethyl 3,3-dimethyl-4-oxo-1-pyrrolidinecarboxylate (1.1321 g, 79%) as a colorless oil. LCMS: (M+Na)+: 270.4.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified directly by silica gel chromatography (20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e302819fe44b42ecaf77840d4f2bb6ca
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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