Methyl morpholine oxide → benzyl (2S)-2-isopropyl-3-oxopyrrolidine-1-carboxylate
Reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C@H:3]1[CH:17]([CH3:19])[CH3:18].C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.C(#N)C>[CH:17]([C@H:3]1[C:2](=[O:1])[CH2:6][CH2:5][N:4]1[C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])([CH3:19])[CH3:18]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution (26 mL) of benzyl (2S)-3-hydroxy-2-isopropylpyrrolidine-1-carboxylate (3.22 g) in dehydrating acetonitrile were added molecular sieves 4A powder (2.31 g) and 4-methylmorpholine-N-oxide (2.86 g), and the mixture was cooled to 0° C. tetra-n-Propylammonium perruthenate (0.16 g) was added, and the mixture was stirred at 0° C. for 1 hr and at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in ethyl acetate. The insoluble material was filtered through Hyflo Super-Cel. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→4:1) to give the title compound as colorless oil (yield: 2.74 g).
Workup
- additionwas added
- concentrationThe reaction mixture was concentrated under reduced pressure
- filtrationThe insoluble material was filtered through Hyflo Super-Cel
- concentrationThe filtrate was concentrated under reduced pressure
- customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→4:1)
Sources & evidence
- ORD record
- ord-e71c75ba89ba4e39aa10e99bb7feae3e
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08013008B2
Reaction notes
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