Sodium hydride → (1-{2-[5-(4-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl)-2-methyl-propyl)-carbamic acid methyl ester

https://huagongshe.com/ja/reaction/79735

関与物質

役割	名称	HCID	仕込み量
反応物	Sodium hydride	HCID 24758	—
反応物	2-Chloromethyl 2-(trimethylsilyl)ethyl ether	HCID 2724271	—
反応物	Methyl (1-(2-(4-(4-bromophenyl)-1H-imidazol-2-YL)pyrrolidin-1-YL)-3-methyl-1-oxobutan-2-YL)carbamate	HCID 66620141	—
溶媒	Dimethylformamide	HCID 6228	—
溶媒	Ethyl Acetate	HCID 8857	—
溶媒	Ammonium Chloride	HCID 25517	—
生成物	(1-{2-[5-(4-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl)-2-methyl-propyl)-carbamic acid methyl ester	HCID 66620156	71.4%

反応手順

(1-{2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (2.6 g, 5.8 mmol) in DMF (60 mL) was treated with NaH (60% dispersion in mineral oil, 256 mg, 6.4 mmol) in one portion. After 5 min, the mixture was treated with SEMCl (1.08 mL, 6.1 mmol) in 0.1 mL portions over 10 min. The reaction was stirred for 2 hours and diluted with saturated NH4Cl solution (50 mL) and EtOAc (100 mL). The organic layer was washed with H2O (3 50 mL) and brine (50 mL). The solution was dried over MgSO4 and subjected to a 120 g SiO2 COMBIFLASH column (0-100% EtOAc-hexanes gradient) to afford (1-{2-[5-(4-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (2.4 g, 71%).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08841278B2
出典データセット	uspto-grants-2014_09
ORD ID	ord-35694f47489f474a81447ed8d97d8635
出典メモ	uspto-grants-2014_09