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Ethyl Acetate → 4-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]2-methyl-2-hydroxybutane fumarate

HRID 233215
ノート
印刷プレビュー

反応式

HRID 233215 の反応式
[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]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21959991Ethyl 3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)1-piperidinyl]propionateHCID 178418573HCID 178418573、化合物

生成物 1

HCID 219601024-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]2-methyl-2-hydroxybutane fumarate

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

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.

後処理

  1. washwas washed with water and brine
  2. customThe organic solution was separated
  3. dry with materialdried over MgSO4
  4. customAfter removal of solvent
  5. customthe crude product was purified by flash chromatography (25 g, SiO2 ; eluted with 1 CH3OH:99 DCM)
  6. customThe material thus purified
  7. customRecrystallization from ethanol yielded white crystals, 2.47 g, m.p.=156°-158° C.

出典と根拠

ORDレコード
ord-4af69fa41b1f4e629431e6a7c7e9d43d
出典データセット
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05591745

反応ノート

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