4-Methylmorpholine → Tert-butyl 2-[[(4-bromobenzoyl)amino]methyl]pyrrolidine-1-carboxylate

関与物質

役割	名称	HCID	仕込み量
反応物	4-Methylmorpholine	HCID 7972	—
反応物	4-Bromobenzoic acid	HCID 11464	—
反応物	(+-)-2-(Aminomethyl)-1-N-Boc-pyrrolidine	HCID 2756484	—
反応物	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	Tert-butyl 2-[[(4-bromobenzoyl)amino]methyl]pyrrolidine-1-carboxylate	HCID 58185404	100%

反応手順

To 2-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.00 g, 4.97 mmol) and 4-bromo-benzoic acid (996 mg, 4.97 mmol) in DMF (25 mL) was added N-methylmorpholine (655 μl, 5.96 mmol) and HATU (1.89 g, 4.97 mmol). After stirring for 3 hours the reaction was concentrated then diluted with EtOAc and washed with 1N HCl, saturated NaHCO3, and brine. The organic phase was then dried over Na2SO4 and concentrated. The crude material was purified by silica gel chromatography (20-50% EtOAc-hexanes gradient) to afford 2-[(4-bromo-benzoylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.91 g, 4.97 mmol, quantitative yield). LCMS-ESI+: calc'd for C17H24BrN2O3: 383.1 (M+H+). Found: 383.6 (M+H+).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08088368B2
出典データセット	uspto-grants-2012_01
ORD ID	ord-b29cdb7a02664df1a136636adc6ea499
出典メモ	uspto-grants-2012_01