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

HRID 877705Notes

Reaction equation

HRID 877705 reaction equation
[OH:1][CH: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>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[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

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 68291226Benzyl 4-hydroxy-3,3-dimethylpyrrolidine-1-carboxylate

Product 1

HCID 66936222Benzyl 3,3-dimethyl-4-oxopyrrolidine-1-carboxylateYield 72.4%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A suspension of benzyl 4-hydroxy-3,3-dimethylpyrrolidine-1-carboxylate (4.07 g, 16.3 mmol) in acetonitrile (50 mL), was added 4-methylmorpholine-4-oxide (3.82 g, 32.7 mmol) and tetrapropylammonium perruthenate (0.42 mL, 1.63 mmol). The mixture was stirred at rt for 18 h. The reaction was concentrated and purified using silica gel chromatography, eluting with 0-30% ethyl acetate in hexanes. Benzyl 3,3-dimethyl-4-oxopyrrolidine-1-carboxylate (2.92 g, 68% yield) was obtained as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.49-7.31 (m, 5H), 5.19 (s, 2H), 3.93 (br. s., 2H), 3.61 (s, 2H), 1.17 (s, 6H); MS (ES+) m/z: 248.1 (M+H); LC retention time: 3.24 min (analytical HPLC Method I).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified
  3. washeluting with 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-90a4cd3caa5d4639adac2861061f4b52
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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