Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 20741434 | HCID 20741434 | — |
| Reactant | HCID 178418255 | HCID 178418255 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 60123706 | HCID 60123706 | 89% |
Reaction Steps
In an atmosphere of nitrogen, phenylmagnesium bromide (3 N diethyl ether solution, 15 ml) was added dropwise to tetrahydrofuran solution (50 ml) of N-methyl-N-methoxy-1-[1-(R)-phenylethyl]-5-oxopyrrolidine-3-(R)-carboxamide (2.49 g, 9.0 mmol), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was mixed with 1 N hydrochloric acid (50 ml) under ice-cooling and extracted with ethyl acetate (8 ml×2). The organic layer was washed with saturated brine (100 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and the residue was subjected to a silica gel column chromatography. By eluting with n-hexane:ethyl acetate (1:1), 2.36 g (89%) of the title compound was obtained as a light yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06825353B2 |
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| Source dataset | uspto-grants-2004_11 |
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| ORD ID | ord-f168abc1d3fa4c5bb7048ecbdcfe9ad1 |
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| Source note | uspto-grants-2004_11 |
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