2-(2-Fluorophenyl)ethylamine → tert-butyl (4S,5R)-2-[2-(2-fluorophenyl)ethylamino]-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	2-(2-Fluorophenyl)ethylamine	HCID 643357	—
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-[2-(2-fluorophenyl)ethylamino]-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate	HCID 68570675	43.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of intermediate 59 (0.5 g, 1.36 mmol), 2-fluorophenethylamine (0.531 mL, 4.07 mmol) and MeOH (0.1 mL) is heated at 100° C. for 3 days. The reaction mixture is cooled to RT, and is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (70:30-60:40) gives 0.27 g of the product 91. 1H NMR (CDCl3) δ 7.40-6.85 (m, 13 H), 6.80-6.65 (m, 2 H), 5.45-5.25 (m, 2 H), 3.90-3.60 (m, 2 H), 1.15 (s, 9 H); MS: m/z 460 (M++1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07741493B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-2e418219514540dd961e1824b9b94156
Source note	uspto-grants-2010_06