Sodium Azide → [5-(3-Azido-phenyl)-5-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester

関与物質

役割	名称	HCID	仕込み量
反応物	Sodium Azide	HCID 33557	—
反応物	1-N,2-N-dimethylcyclohexane-1,2-diamine	HCID 551074	—
反応物	Sodium Ascorbate	HCID 23667548	—
反応物	HCID 66665441	HCID 66665441	—
触媒	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
溶媒	Ethanol	HCID 702	—
溶媒	Water	HCID 962	—
生成物	[5-(3-Azido-phenyl)-5-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester	HCID 86650252	—

反応条件

温度	90 °C

反応手順

A suspension of [5-(3-bromo-phenyl)-5-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (114 mg, 0.295 mmol), NaN3 (77 mg, 1.18 mmol), CuI (11 mg, 0.059 mmol), sodium ascorbate (12 mg, 0.059 mmol), N,N′-dimethyl-cyclohexane-1,2-diamine (13 mg, 0.089 mmol), 1.5 ml of EtOH and 0.6 ml of water was stirred under N2 at 90° C. for 1 h. The mixture was filtered through Celite, and the filtrate was chromatographed on silica gel (cyclohexane/EtOAc=6:1) to yield the title compound in the form of a colourless foam. TLC (hexane/EtOAc=3:1): Rf=0.33; HPLC: RtH1=2.258 min; 1H-NMR (400 MHz, CDCl3); 7.40-6.88 (m, 4H; broad signals due to rotamers), 4.75-3.60 (m, 6H), 1.42 (br, 9H); MS: 350 [(M+H)+].

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08846658B2
出典データセット	uspto-grants-2014_09
ORD ID	ord-67af881384a140ab88b90ebf61602208
出典メモ	uspto-grants-2014_09