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Sodium Carbonate → 2-tert-Butoxy-3-[2-[4-(2-fluorophenoxymethyl)piperidino)ethyl]pyrazine

HRID 914871
ノート
印刷プレビュー

反応式

HRID 914871 の反応式
[C:1]([O:5][C:6]1[C:11](/[CH:12]=[CH:13]\OC)=[N:10][CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[F:17][C:18]1[CH:31]=[CH:30][CH:29]=[CH:28][C:19]=1[O:20][CH2:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C(OCC)(=O)C>[C:1]([O:5][C:6]1[C:11]([CH2:12][CH2:13][N:25]2[CH2:24][CH2:23][CH:22]([CH2:21][O:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[F:17])[CH2:27][CH2:26]2)=[N:10][CH:9]=[CH:8][N:7]=1)([CH3:2])([CH3:3])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 171780504-((2-Fluorophenoxy)methyl)piperidine hydrochlorideHCID 67047587(Z)-2-tert-butoxy-3-(2-methoxyvinyl)pyrazine

生成物 1

HCID 222478612-tert-Butoxy-3-[2-[4-(2-fluorophenoxymethyl)piperidino)ethyl]pyrazine収率 10.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

After adding 139 mg of (Z)-2-tert-butoxy-3-(2-methoxyvinyl)pyrazine and 196 mg of 4-(2-fluorophenoxymethyl)piperidine hydrochloride in 5 ml of dichloromethane, 213 mg of sodium triacetoxyborohydride was added and the mixture was stirred overnight at room temperature. Aqueous sodium carbonate solution was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (26 mg, 10% yield).

後処理

  1. additionwas added
  2. washThe organic layer was washed with water and saturated brine in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-70668521291d428a9e88092522c8e7e7
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07265108B2

反応ノート

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