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:18])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[CH3:24][Mg]Br.[NH4+].[Cl-].CC[O:31][C:32]([CH3:34])=[O:33]>O1CCCC1>[C:32]([OH:33])(=[O:31])/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18].[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:32]([CH3:34])([OH:33])[CH3:24])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1참가 물질
반응물 4
생성물 1
시약·촉매·용매 1
실험 절차
To a solution of ethyl 3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propionate (3.21 g, 10 mmol) in tetrahydrofuran (THF, 100 ml), was added methylmagnesium bromide (10 ml, 30 mmol, 3M solution in ether) dropwise over 15 minutes at room temperature under N2. The resulting mixture was stirred for 16 hours. The mixture was slowly hydrolyzed with aqueous NH4Cl solution. The THF solution was diluted with EtOAc (300 ml), then was washed with water and brine. The organic solution was separated and dried over MgSO4. After removal of solvent, the crude product was purified by flash chromatography (25 g, SiO2 eluted with 1 CH3OH:99 DCM). The material thus purified weighed 2.36 g (77%) as white crystals. This was converted to the fumarate salt by treatment with fumaric acid (895 mg) in ethanol. Recrystallization from ethanol yielded white crystals, 2.47 g, m.p.=156°-158° C.
후처리
- washwas washed with water and brine
- customThe organic solution was separated
- dry with materialdried over MgSO4
- customAfter removal of solvent
- customthe crude product was purified by flash chromatography (25 g, SiO2 eluted with 1 CH3OH:99 DCM)
- customThe material thus purified
- customRecrystallization from ethanol yielded white crystals, 2.47 g, m.p.=156°-158° C.
출처 및 근거
- ORD 기록
- ord-87c2070b9c344663b26d342992734c33
- 출처 데이터셋
- uspto-grants-1997_07
- 특허 번호
- US05646161
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