HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 1-Benzyl-4-[tert-butoxycarbonyl-(benzyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Benzaldehyde | HCID 240 | — |
| Reactant | Sulfuric acid magnesium salt (1:1) | HCID 24083 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 67547185 | HCID 67547185 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-Benzyl-4-[tert-butoxycarbonyl-(benzyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester | HCID 67548815 | — |
Reaction Steps
To a solution of (10) and a benzaldehyde (unsubstituted or substituted by R1) in DCM are added MgSO4, AcOH, and then NaBH3CN. The reaction mixture is stirred overnight, and then diluted with DCM. The organic solution is washed with NaHCO3, dried and concentrated. The residue is dissolved in water, treated with (Boc)2O, and then stirred overnight. The reaction mixture is extracted with DCM, dried, and concentrated to give product 1-benzyl-4-[tert-butoxycarbonyl-(benzyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester (11).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07528136B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-2b82d28d78c64a06a469eeb4324a65d3 |
| Source note | uspto-grants-2009_05 |