Reaction equation
[C:1]([N:6]1[C@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][O:8][C:7]1=[O:17])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:18](O)(C(F)(F)F)=O.[CH2:25]([N:32](C[Si](C)(C)C)[CH2:33]OC)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[CH2:25]([N:32]1[CH2:33][CH2:4][C@:2]([CH3:18])([C:1]([N:6]2[C@H:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:9][O:8][C:7]2=[O:17])=[O:5])[CH2:3]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (R)-3-methacryloyl-4-phenyloxazolidin-2-one (135.00 g, 583.79 mmol) and TFA (4.497 mL, 58.379 mmol) in dry toluene (50 mL) at <10° C. was quickly added dropwise N-benzyl-1-methoxy-N-((trimethylsilyl)methyl)methanamine (194.16 mL, 758.93 mmol), and the mixture was stirred at ambient temperature overnight. The reaction was filtered and the filtrate was extracted with 4N HCl (3×250 mL). The aqueous layer was washed with ethyl acetate (250 mL) then made basic with solid K2CO3 to pH 10. The basic aqueous layer was extracted with ethyl acetate (4×400 mL), dried (MgSO4), filtered and concentrated under reduced pressure to provide (R)-3-((S)-1-benzyl-3-methylpyrrolidine-3-carbonyl)-4-phenyloxazolidin-2-one (145 g, 399 mmol, 68% yield) as a dark oil.
Workup
- filtrationThe reaction was filtered
- extractionthe filtrate was extracted with 4N HCl (3×250 mL)
- washThe aqueous layer was washed with ethyl acetate (250 mL)
- extractionThe basic aqueous layer was extracted with ethyl acetate (4×400 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-02446b8d51614e65beb02f4f717ac37d
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889704B2
Linked notes
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