HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isocyanate → [(R)-1-((R)-1-Benzyl-pyrrolidin-3-ylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isocyanate | HCID 105034 | — |
| Reactant | (3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine | HCID 1514397 | — |
| Reactant | ((R)-1-Benzyl-pyrrolidin-3-yl)-carbamic acid 4-nitro-phenyl ester | HCID 68443154 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | [(R)-1-((R)-1-Benzyl-pyrrolidin-3-ylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester | HCID 67022985 | — |
Reaction Steps
A solution of ((R)-1-benzyl-pyrrolidin-3-yl)-carbamic acid 4-nitro-phenyl ester (1 eq.) and (3R)-(+)-3-(Boc-amino)pyrrolidine in MeOH is heated using microwave radiation at 100° C. for 1 hour. The reaction mixture is reduced in vacuo. The resulting oil is dissolved in DCM and isocyanate resin (3 eq.) is added and shaken overnight. The resin was filtered off and the DCM was removed in vacuo to yield the title compound. MS (ES+) m/e 299.21 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08188100B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-dd1f195f8cfc4bd382fdb8eb0993647c |
| Source note | uspto-grants-2012_05 |