3-Fluorobenzylamine → tert-butyl (4S,5R)-2-[(3-fluorophenyl)methylamino]-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate

https://huagongshe.com/reaction/2053528

Participants

Role	Name	HCID	Charge
Reactant	3-Fluorobenzylamine	HCID 66853	—
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-[(3-fluorophenyl)methylamino]-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate	HCID 68569694	62.1%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of intermediate 59 (2.0 g, 5.42 mmol), 3-fluorobenzylamine (1.86 mL, 16.2 mmol) and MeOH (0.5 mL) is heated at 100° C. for 2 days. The reaction mixture is cooled to RT, and is purified twice by chromatography on silica gel; gradient elution with heptane:EtOAc (70:30-60:40) gives 1.5 g of the product 87. 1H NMR (CDCl3) δ 7.50 (s, 1H), 7.40-7.30 (m, 1H), 7.30-7.15 (m, 2H), 7.10-6.90 (m, 9H), 7.85-7.75 (m, 2H), 5.50-5.30 (m, 2H), 4.80-4.55 (m, 2H), 1.15 (s, 9H); MS: m/z 446 (M++1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07326792B2
Source dataset	uspto-grants-2008_02
ORD ID	ord-352bc8b5946647b4990ee9a58dab3312
Source note	uspto-grants-2008_02