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]([O:19]CC)=O)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[CH2:24]([Mg][Cl:28])[CH2:25][CH3:26].[CH2:29]1[CH2:33]OC[CH2:30]1>>[ClH:28].[F:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][C:17]([OH:19])([CH2:30][CH2:29][CH3:33])[CH2:24][CH2:25][CH3:26])[CH2:13][CH2:14]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 (4.5 g, 14.0 mmol) in THF (120 ml) was added propylmagnesium chloride (21.1 ml, 42.0 mmol, 2.0M 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., 30 ml). The layers were separated and the aqueous phase was extracted with EtOAc (2X). 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, 2% Et3N/ether). After flushing the product through alumina with ether, the hydrochloride salt was prepared in ether/EtOAc (1:1, 40 ml, 1 drop IPA) with ethereal HCl to give 2.5 g (45%) of the desired product as a white solid, m.p.=163°-164° C.
후처리
- customwas carefully quenched with NH4Cl (sat., 30 ml)
- customThe layers were separated
- extractionthe aqueous phase was extracted with EtOAc (2X)
- 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, 2% Et3N/ether)
- customAfter flushing the product through alumina with ether
출처 및 근거
- ORD 기록
- ord-73e55ab4b3564175ba3e85146c1f22e4
- 출처 데이터셋
- uspto-grants-1997_01
- 특허 번호
- US05591745
연결된 노트
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