HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopropylamine → [(R)-1-(5-Bromo-pyridin-2-yl)-pyrrolidin-3-yl]-cyclopropyl-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | methanesulfonic acid (S)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-yl ester | HCID 86638154 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | [(R)-1-(5-Bromo-pyridin-2-yl)-pyrrolidin-3-yl]-cyclopropyl-amine | HCID 66673109 | 61.2% |
Reaction Steps
Dissolve methanesulfonic acid (S)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-yl ester (3.07 g, 9.48 mmol) and cyclopropylamine (1.7 mL, 23.68 mmol) in THF (20 mL). Microwave the mixture at 130° C. for 6 h. Dilute the mixture with EtOAc (100 mL) and wash with saturated NaHCO3 (25 mL). Dry the organic portion over Na2SO4, filter, and concentrate. Purify the crude material by chromatography, eluting with a gradient of 75-100% EtOAc/hexane to give 1.638 g (61%) of the title compound. LC-MS/ES m/z (79Br) 283.0 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08101764B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-745b8b3e18d846b79c855d0f8f90b2f4 |
| Source note | uspto-grants-2012_01 |