Cyclopentylamine → (R)-tert-butyl 1-(cyclopentylamino)-3-hydroxy-3-methyl-1-oxobutan-2-ylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Cyclopentylamine	HCID 2906	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	N-(tert-Butoxycarbonyl)-3-hydroxy-D-valine	HCID 11299247	—
Solvent	Dichloromethane	HCID 6344	—
Product	(R)-tert-butyl 1-(cyclopentylamino)-3-hydroxy-3-methyl-1-oxobutan-2-ylcarbamate	HCID 67224582	93.2%

Reaction Steps

To a mixture of (R)-2-(tert-butoxycarbonylamino)-3-hydroxy-3-methylbutanoic acid (0.5 g, 2.144 mmol), HATU (0.978 g, 2.57 mmol) and cyclopentanamine (0.423 mL, 4.29 mmol) in DCM (10 mL) was added Et3N (0.598 mL, 4.29 mmol). The reaction mixture was stirred at room temperature for 5 h and then washed with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4, concentrated, and purified by silica column chromatography (MeOH/DCM, 0-10%) to afford the title compound (0.6 g, 93%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08785429B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-5ef701cb47ca4bc7aea7b38dc48f1fb5
Source note	uspto-grants-2014_07