Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methyl 2,3-dibromopropionate | HCID 95428 | — |
| Reactant | HCID 8027396 | HCID 8027396 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 66927008 | HCID 66927008 | 45.9% |
Reaction Steps
To a suspension of 1-phenyl-N-[(2R)-pyrrolidin-2-ylmethyl]methanamine (13.6 g) in toluene (120 mL) were added triethylamine (22.9 mL) and methyl 2,3-dibromopropanoate (13.4 g) under ice-cooling, and the mixture was stirred with heating at 90° C. for 5 hr. The reaction mixture was allowed to cool to room temperature, and diluted with diethyl ether (200 mL) and brine (200 mL). The organic layer was dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and purified by silica gel column chromatography (ethyl acetate/hexane=10/80→50/50) to give the title compound (6.86 g) as a pale-yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09388195B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-faf9e1ec4ba94f488a660e49add52341 |
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| Source note | uspto-grants-2016_07 |
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