Dichloromethane → (R)-2-Cyclopentyl-1-(4-dimethylaminopiperidin-1-yl)-2-hydroxy-2-phenylethanone

関与物質

役割	名称	HCID	仕込み量
反応物	Dichloromethane	HCID 6344	—
反応物	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
反応物	1-Hydroxybenzotriazole	HCID 75771	—
反応物	Diisopropylethylamine	HCID 81531	—
反応物	N,N-Dimethylpiperidin-4-amine	HCID 417391	—
反応物	alpha-Cyclopentylmandelic acid, (+)-	HCID 948620	—
生成物	(R)-2-Cyclopentyl-1-(4-dimethylaminopiperidin-1-yl)-2-hydroxy-2-phenylethanone	HCID 59828529	60%

反応手順

To a stirred solution of (R)-cyclopentylhydroxyphenyl acetic acid (5.00 g, 22.7 mmol) in DCM (200 mL, 3 mol) was added dimethylpiperidin-4-yl amine (2.91 g, 22.7 mmol). DIPEA (11.9 mL, 68.1 mmol) and HOBt (5.21 g, 34 mmol) were added, followed by EDCI (5.22 g, 27.2 mmol). The mixture was stirred for 12 hours, then washed with water (300 mL), a saturated aqueous NaCl solution (300 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure. The crude material was purified via silica gel chromatography (10% MeOH/DCM w/1% NH3 (aq)) to afford 4.5 g of the title compound.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08492407B2
出典データセット	uspto-grants-2013_07
ORD ID	ord-36a7bcd5d5f845e0a187bbda190976ac
出典メモ	uspto-grants-2013_07