Toluene → N-[(1S)-1-(4-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl)phenyl)-ethyl]cyclopropanecarboxamide

関与物質

役割	名称	HCID	仕込み量
反応物	Toluene	HCID 1140	—
反応物	N-[(1S)-1-(4-bromophenyl)ethyl]cyclopropanecarboxamide	HCID 800360	—
反応物	Sodium t-butoxide	HCID 23676156	—
反応物	3-[3,5-Bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidine	HCID 53262186	—
触媒	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
触媒	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
溶媒	Ethyl Acetate	HCID 8857	—
生成物	N-[(1S)-1-(4-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl)phenyl)-ethyl]cyclopropanecarboxamide	HCID 53261930	100%

反応手順

To a reaction vessel, N-[(1S)-1-(4-bromophenyl)ethyl]cyclopropanecarboxamide (134 mg), 3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidine (211 mg), sodium t-butoxide (96 mg), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (10 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (18 mg) and toluene (6 ml) were added, and reacted in a microwave reactor (Initiator™, manufactured by Biotage) for 10 minutes at 120° C. Upon the completion of the reaction, ethyl acetate was added and the precipitates were filtered by using silica gel. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to obtain N-[(1S)-1-(4-{3-[3,5-bis-(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}phenyl)ethyl]cyclopropanecarboxamide (269 mg). 1H-NMR (CDCl3) as given in Table 2

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08536201B2
出典データセット	uspto-grants-2013_09
ORD ID	ord-f0e75c6ea85a4164a3dc0950d8405866
出典メモ	uspto-grants-2013_09