Benzylamine → tert-butyl (4S,5R)-2-(benzylamino)-4,5-bis(4-fluorophenyl)-4,5-dihydroimidazole-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Benzylamine	HCID 7504	—
Reactant	4-Fluorophenyl-2-methylthio-4,5-dihydro-imidazole-1-carboxylic Acid, Tert-Butyl Ester	HCID 86596323	—
Solvent	Methanol	HCID 887	—
Product	tert-butyl (4S,5R)-2-(benzylamino)-4,5-bis(4-fluorophenyl)-4,5-dihydroimidazole-1-carboxylate	HCID 68570645	123.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of intermediate 62 (0.5 g, 1.24 mmol), benzylamine (0.680 mL, 6.2 mmol) and MeOH (0.1 mL) is heated at 100° C. overnight. The reaction mixture is cooled to RT and purified by chromatography on silica gel; gradient elution with heptane:EtOAc (75:25-60:40) gives 0.354 g of the product 160. 1H NMR (CDCl3) δ 7.55-7.25 (m, 6 H), 6.95-6.85 (m, 2 H), 6.80-6.60 (m, 6 H), 5.45-5.20 (m, 2 H), 4.75-4.55 (m, 2 H), 1.16 (s, 9 H)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07741493B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-5a306d0da0c444a7b25fbf0a86f330e8
Source note	uspto-grants-2010_06