Diisopropylethylamine → Methyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidine-1-yl)methyl]cyclopentanecarboxylate

https://huagongshe.com/ja/reaction/736413

関与物質

役割	名称	HCID	仕込み量
反応物	Diisopropylethylamine	HCID 81531	—
反応物	Tert-butyl (piperidin-4-ylmethyl)carbamate	HCID 723429	—
反応物	1-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}cyclopentanecarboxylic acid	HCID 11510532	—
溶媒	N-methyl-2-pyrrolidone	HCID 13387	—
溶媒	Sodium Bicarbonate	HCID 516892	—
生成物	Methyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidine-1-yl)methyl]cyclopentanecarboxylate	HCID 67232469	67.2%

反応条件

温度	120 °C

反応手順

A mixture of Methyl 1-(iodomethyl)cyclopentanecarboxylate (5.52 g, 0.0206 mol, Step 1), tert-butyl (piperidin-4-ylmethyl)carbamate (8.83 g, 0.0412 mol) and iPr2NEt (10.76 mL, 0.0618 mol) in N-methylpyrrolidone (70 mL) was stirred at 120° C. for 24 h. After cooling, the reaction mixture was diluted with sat. NaHCO3 aq. (200 mL), extracted with AcOEt (200 mL) for three times, and the combined organic layer was washed with water (200 mL) and brine (200 mL). The organic layer was dried over Na2SO4, filtered and concentrated. Removal of the solvent gave a residue, which was chromatographed on a column of silica gel eluting with EtOAc/hexane (1:1) to give 4.91 g (67%) of title compound as a yellow syrup.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07595329B2
出典データセット	uspto-grants-2009_09
ORD ID	ord-df2cbae2cf924e569589faf7c96324f7
出典メモ	uspto-grants-2009_09