반응식
[F:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17](OCC)=[O:18])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[CH2:24]([Mg]Br)[CH3:25].[CH2:28]1COC[CH2:29]1>>[F:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]([OH:18])([CH2:24][CH3:25])[CH2:28][CH3:29])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1참가 물질
실험 절차
To a solution of ethyl 3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propionate (3.9 g, 12.0 mmol) in THF (100 ml) was added ethylmagnesium bromide (12.0 ml, 36.0 mmol, 3.0M in ether) at room temperature under nitrogen (mild exotherm). The reaction mixture was stirred for 17 hours at which time it was carefully quenched with NH4Cl (sat., 20 ml). The precipitated salts were dissolved into water (25 ml) and the layers were separated. The aqueous phase was extracted with EtOAc (2×) and the combined organics were washed with brine and dried (Na2SO4). Filtration and concentration gave the crude product which was purified via flash column chromatography (silica gel, 1% MeOH/DCM) to give 2.4 g (61%) of the desired product as an oil which solidified on standing, m.p.=50°-53° C.
후처리
- customwas carefully quenched with NH4Cl (sat., 20 ml)
- dissolutionThe precipitated salts were dissolved into water (25 ml)
- customthe layers were separated
- extractionThe aqueous phase was extracted with EtOAc (2×)
- washthe combined organics were washed with brine
- dry with materialdried (Na2SO4)
- filtrationFiltration and concentration
- customgave the crude product which
- customwas purified via flash column chromatography (silica gel, 1% MeOH/DCM)
출처 및 근거
- ORD 기록
- ord-10e4689ecca34ad2b7a83b2c655a04ea
- 출처 데이터셋
- uspto-grants-1997_01
- 특허 번호
- US05593995
연결된 노트
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