HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyrrolidine → 1′-(1,1-Dimethylethyl) 5′-methyl [1,3′-bipyrrolidine]-1′,5′-dicarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester | HCID 613145 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 1-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate | HCID 10988485 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1′-(1,1-Dimethylethyl) 5′-methyl [1,3′-bipyrrolidine]-1′,5′-dicarboxylate | HCID 69817351 | 83.8% |
Reaction Steps
To a solution of N-t-butoxycarbonyl-4-oxo-L-proline methyl ester (1.0 g, 4 mmol) (J. Org. Chem. 2001, 10, 3593), pyrrolidine (0.4 ml, 5 mmol), acetic add (0.3 ml, 5 mmol) in CH2Cl2 (20 ml) was added sodium triacetoxyborohydride (1.0 g, 5 mmol) and the mixture stirred for 2 h. After which time it was washed with saturated sodium hydrogen carbonate, dried (Na2SO4) and concentrated. Flash column chromatography (EtOAc:MeOH 95:5) afforded the title compound (1.0 g, 81%) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07977358B2 |
| Source dataset | uspto-grants-2011_07 |
| ORD ID | ord-a620527c7cf640c9be0760560488e1cc |
| Source note | uspto-grants-2011_07 |