N,N'-Dimethylethylenediamine → tert-butyl N-[(3S)-1-(6-chloro-3-fluoro-2-pyridyl)-3-piperidyl]carbamate
Reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][C@H:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:11]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I>[Cl:9][C:4]1[N:3]=[C:2]([N:10]2[CH2:15][CH2:14][CH2:13][C@H:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:11]2)[C:7]([F:8])=[CH:6][CH:5]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 105 °C
Procedure
A mixture of 2,6-dichloro-3-fluoro-pyridine (3.802 mmol, 631.1 mg), tert-butyl N-[(3S)-3-piperidyl]carbamate (3.992 mmol; 799.6 mg), potassium carbonate (7.605 mmol; 1051 mg), N,N′-Dimethylethylenediamine (0.3802 mmol; 33.52 mg; 0.0409 mL), and copper(I) iodide; (3.802 mmol; 724.1 mg) in 1,4-Dioxane (15 mL) was purged with Argon then sealed in a pressure tube and heated at 105° C. overnight. The reaction was cooled to room temperature, then filtered through Celite. The filtrate was concentrated and the residue was purified on silica eluted with 0 to 20% EtOAc in Heptane to afford tert-butyl N-[(3S)-1-(6-chloro-3-fluoro-2-pyridyl)-3-piperidyl]carbamate (279.2 mg, 22%) as a white solid.
Workup
- custom(3.802 mmol; 724.1 mg) in 1,4-Dioxane (15 mL) was purged with Argon
- customthen sealed in a pressure tube
- temperatureThe reaction was cooled to room temperature
- filtrationfiltered through Celite
- concentrationThe filtrate was concentrated
- customthe residue was purified on silica
- washeluted with 0 to 20% EtOAc in Heptane
Sources & evidence
- ORD record
- ord-cafc43eae2df48868f8979638c3b6792
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434725B2
Reaction notes
Loading…