Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | HCID 60209506 | HCID 60209506 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 60209507 | HCID 60209507 | 98.3% |
Reaction Steps
Sodium cyanide (4.3 g, 87.4 mmol) was added to a solution of crude (2S,4R)-4-(3,4-dichlorobenzyl)-1-tert-butoxycarbonyl-2-(methanesulfonyloxymethyl)pyrrolidine (7.7 g, 17.5 mmol) in dry DMSO (120 mL) and the mixture was heated at 80° C. with stirring for 3.5 hrs. The reaction mixture was cooled and worked up between EtOAc and aqueous Na2CO3. Vacuum drying of the product afforded 6.34 g (17.2 mmol) of (2S,4R)-2-(cyanomethyl)-4-(3,4-dichloro-benzyl)-1-tert-butoxycarbonylpyrrolidine as an amber oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06552028B2 |
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| Source dataset | uspto-grants-2003_04 |
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| ORD ID | ord-1eadaafdc2fb478f819e6ae25aea7d33 |
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| Source note | uspto-grants-2003_04 |
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