HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → tert-Butyl [(3S)-1-({1-[6-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}carbonyl)pyrrolidin-3-yl]carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-Chloro-6-(trifluoromethyl)pyridine | HCID 602334 | — |
| Reactant | tert-butyl [(3S)-1-(piperidin-4-ylcarbonyl)pyrrolidin-3-yl]carbamate | HCID 57803247 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | tert-Butyl [(3S)-1-({1-[6-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}carbonyl)pyrrolidin-3-yl]carbamate | HCID 57803327 | 29.7% |
Reaction Steps
A solution of 2-chloro-6-(trifluoromethyl)pyridine (1.8 g, 9.9 mmol), tert-butyl [(3S)-1-(piperidin-4-ylcarbonyl)pyrrolidin-3-yl]carbamate (2.97 g, 10.0 mmol) and triethylamine (4.1 mL, 30 mmol) in DMF (50 mL) was heated at 100° C. for 4 hrs. After cooling down, ethyl acetate was added. The resulting solution was washed with brine several times, dried over Na2SO4 and concentrated. The residue was chromatographed on silica gel to give the title compound (1.3 g) as a yellow solid. MS (M+H) 443.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08697870B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-0259c53cb69d4ade8e1532a340f8e912 |
| Source note | uspto-grants-2014_04 |