Diisopropylethylamine → [(R)-2-(4-cyanopiperidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-carbamic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-Cyanopiperidine	HCID 138223	—
Reactant	(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acid	HCID 7146275	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Dimethylformamide	HCID 6228	—
Product	[(R)-2-(4-cyanopiperidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-carbamic acid tert-butyl ester	HCID 71279447	105.8%

Reaction Steps

In a round-bottomed flask, Boc-D-cyclopropylglycine (1.80 g, 8.36 mmol) and piperidine-4-carbonitrile (1.2 g, 10.9 mmol) were dissolved in DMF (30 ml). HATU (3.5 g, 9.2 mmol) and N,N-diisopropylethylamine (2.3 ml, 13.2 mmol) were added and the yellow solution was stirred at room temperature overnight. The reaction mixture was quenched with water and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated to afford 2.72 g (95%) of [(R)-2-(4-cyanopiperidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-carbamic acid tert-butyl ester as a light yellow oil which was used without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08658646B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-ef25d518cf304bf8aa9d2ac356694a1f
Source note	uspto-grants-2014_02