N,N'-Dimethylethylenediamine → tert-butyl N-[(3S)-1-(6-chloro-3-methyl-2-pyridyl)-6-oxo-3-piperidyl]carbamate

Participants

Role	Name	HCID	Charge
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(S)-tert-butyl 6-oxopiperidin-3-ylcarbamate	HCID 15466433	—
Reactant	2-Bromo-6-chloro-3-methylpyridine	HCID 53416675	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	tert-butyl N-[(3S)-1-(6-chloro-3-methyl-2-pyridyl)-6-oxo-3-piperidyl]carbamate	HCID 86707113	55.1%

Reaction Conditions

Temperature	110 °C

Reaction Steps

A solution containing 2-bromo-6-chloro-3-methylpyridine (487 mg, 2.24 mmol), tert-butyl N-[(3S)-6-oxo-3-piperidyl]carbamate (400 mg, 1.87 mmol), Copper(I) iodide (356 mg, 1.87 mmol), Potassium carbonate (310 mg, 2.24 mmol) and N,N′-Dimethylethylenediamine (329 mg, 3.73 mmol) in dioxane 12 mL was stirred at 110° C. 18 h. The reaction was filtered through celite and concentrated. The crude product was purified by flash chromatography (EtOAc/Heptane eluted at 50% EtOAc) to give the desired product 350 mg 38% yield. MS (ESI) m/z: 340.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434725B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-56fcae3fe5fa4a4ab12aa5d86af2828e
Source note	uspto-grants-2016_09