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

Participants

Role	Name	HCID	Charge
Reactant	Phenethylamine	HCID 1001	—
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)-4,5-diphenyl-2-(2-phenylethylamino)-4,5-dihydroimidazole-1-carboxylate	HCID 68567764	44.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of intermediate 59 (2.0 g, 5.43 mmol), phenethylamine (2.04 mL, 16.3 mmol) and MeOH (0.5 mL) is heated at 100° C. for 2 days. The reaction mixture is cooled to RT, and is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (75:25-60:40) gives 1.06 g of the product 93. 1H NMR (CDCl3) δ 7.40-7.30 (m, 4 H), 7.30-7.10 (m, 2 H), 7.10-6.90 (m, 8 H), 6.80-6.65 (m, 2 H), 5.45-5.25 (m, 2 H), 3.90-3.60 (m, 2 H), 3.05 (t, 2 H), 1.13 (s, 9 H); MS: m/z 442 (M++1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07741493B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-39aec90ac6334d988d526f16157f5b06
Source note	uspto-grants-2010_06