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

Participants

Role	Name	HCID	Charge
Reactant	Benzylamine	HCID 7504	—
Reactant	cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-imidazole-1-carboxylic Acid, Tert-Butyl Ester	HCID 86596320	—
Solvent	Methanol	HCID 887	—
Product	tert-butyl (4S,5R)-2-(benzylamino)-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate	HCID 68567154	48.3%

Reaction Conditions

Temperature	95 °C

Reaction Steps

A mixture of intermediate 59 (5.0 g, 0.0136 mol), benzylamine (4.5 mL, 0.0407 mol) and MeOH (1 mL) is heated at 95° C. for 2 days. The reaction mixture is cooled to RT and purified by chromatography on silica gel; gradient elution with heptane:EtOAc (80:20-50:50) gives 2.81 g of the product 77. 1H NMR (CDCl3) δ 7.55-7.25 (m, 6 H), 7.10-6.85 (m, 8 H), 6.85-6.70 (m, 2 H), 5.50-5.30 (m, 2 H), 4.80-4.55 (m, 2 H), 1.14 (s, 9 H)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07741493B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-01dbbfe5b97b451ba52719ed5dad67d6
Source note	uspto-grants-2010_06