N-((1S)-1-(4-Bromophenyl)ethyl)acetamide → (S)-N-(1-{4-[3-(tert-Butyl-dimethyl-silanyloxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide

https://huagongshe.com/ko/reaction/40499

참여 물질

역할	이름	HCID	투입량
반응물	N-((1S)-1-(4-Bromophenyl)ethyl)acetamide	HCID 793484	—
반응물	2-(Di-tert-butylphosphino)biphenyl	HCID 2734215	—
반응물	Sodium t-butoxide	HCID 23676156	—
반응물	3-((tert-Butyldimethylsilanyl)oxy)azetidine	HCID 57438656	—
용매	Methanol	HCID 887	—
용매	Water	HCID 962	—
용매	1,4-Dioxane	HCID 31275	—
생성물	(S)-N-(1-{4-[3-(tert-Butyl-dimethyl-silanyloxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide	HCID 86689004	—

반응 조건

온도	80 °C

반응 단계

A mixture of 3.0 g (12.4 mmol) (S)—N-[1-(4-bromo-phenyl)-ethyl]-acetamide (I.1), 2.3 g (12.4 mmol) 3-(tert-butyl-dimethyl-silanyloxy)-azetidine (US2008/214520A1), 4.9 g (97%, 49.6 mmol) NaOtBu, 1.48 g (4.96 mmol) 2-(di-tert-butylphosphino)biphenyl and 1.1 g (1.24 mmol) tris-(dibenzylideneacetone)-dipalladium(0) in 30 mL 1,4-dioxane is stirred for 45 min under microwave irradiation at 80° C. After cooling water and MeOH are added, the mixture is filtered, concentrated in vacuo and directly purified by HPLC (column: XbridgeC18; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08530461B2
출처 데이터셋	uspto-grants-2013_09
ORD ID	ord-dcd68dc0bcee42018476560e3ed1afa3
출처 메모	uspto-grants-2013_09