HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 4-[(3R,4S)-3-(4-Chloro-phenyl)-4-methylamino-pyrrolidine-1-carbonyl]-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | [(3S,4R)-4-(4-Chloro-phenyl)-1-(5'-cyano-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester | HCID 58303011 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 4-[(3R,4S)-3-(4-Chloro-phenyl)-4-methylamino-pyrrolidine-1-carbonyl]-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carbonitrile | HCID 67233823 | 73.2% |
Reaction Steps
To a solution of [(3S,4R)-4-(4-Chloro-phenyl)-1-(5′-cyano-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (3.20 g, 6.12 mmol) in acetonitrile (30 mL) was added at ambient temperature trifluoroacetic acid (4.7 mL, 61.2 mmol) and the reaction mixture was stirred for 4 h at this temperature. After concentration, the residue was dissolved in ethyl acetate and washed with aqueous sodium carbonate (20%). The organic layer was dried over sodium sulfate and concentrated affording the title compound (1.90 g, 73%) as a light yellow foam. MS m/e: 424.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09226916B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-c8c48ba2710e44c0bebc690219d61de6 |
| Source note | uspto-grants-2016_01 |