HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → (R)-3-tert-Butoxycarbonylamino-pyrrolidine-1-carboxylic acid phenyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Phenyl chloroformate | HCID 15891 | — |
| Reactant | (3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine | HCID 1514397 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (R)-3-tert-Butoxycarbonylamino-pyrrolidine-1-carboxylic acid phenyl ester | HCID 67022933 | — |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
Phenyl chloroformate (1 eq.) is added dropwise to a solution of pyridine in DCM. The reaction mixture is cooled to 0° C. and a solution of (R)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (1 eq.) in DCM is added dropwise. The reaction mixture is stirred at RT for 1 hour. The reaction mixture is partitioned between (0.2 M) HCl)(aq) and DCM. The organics are washed with water, (sat)NaHCO3(aq) and brine. The organics are dried (MgSO4), filtered and reduced in vacuo to yield the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08193164B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-993da7804b3a4e1887dccdba46c33c71 |
| Source note | uspto-grants-2012_06 |