Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 86612724 | HCID 86612724 | — |
| Catalyst | Tetrabutylammonium Cyanide | HCID 165872 | — |
| Product | HCID 11334515 | HCID 11334515 | 77.4% |
Reaction Steps
(3S)-1-Diphenylmethyl-3-mesyloxypyrrolidine (1.25 g) was dissolved in acetonitrile (1.75 mL). Tetrabutylammonium cyanide (1.87 g) was added to the solution, and the mixture was stirred at 65° C. for 12 hours. Saturated sodium hydrogencarbonate (7 mL) and toluene were added dropwise to the reaction mixture, whereby the organic layer was extracted. The organic layer was washed with water and then dried over sodium sulfate. The drying agent was removed through filtration, and the filtrate was concentrated under reduced pressure, to thereby yield crystals. The residue was subjected to silica gel chromatography, to thereby give the target compound (0.766 g, yield 77.4%) as colorless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07569599B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-1a32de4539854bbc975567146e1cabfe |
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| Source note | uspto-grants-2009_08 |
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