Water → (1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol

HRID 890067

反応式

HRID 890067 の反応式
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][O:2]1.[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([CH:23]=[O:24])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.C(OCC)(=O)C>O1CCCC1.C([Li])CCC>[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([CH:23]([CH:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][O:2]2)[OH:24])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 103271,3-DihydroisobenzofuranHCID 895841-Benzylpiperidine-4-carbaldehyde

生成物 1

HCID 22248465(1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol収率 37.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 178418339Butyllithium溶媒

反応条件

温度
-70 °C

実験手順

After dissolving 591 mg of 1,3-dihydroisobenzofuran in 10 ml of tetrahydrofuran, 3.9 ml of n-butyllithium (1.5 M, n-hexane solution) was added thereto at −70° C. under a nitrogen atmosphere, the mixture was stirred for 1 hour, and then a solution of 1 g of 1-benzylpiperidine-4-carboxaldehyde in tetrahydrofuran (5 ml) was added dropwise and the mixture was stirred for 1 hour. Water was added to the reaction solution, extraction was performed with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain 597 mg of (1-benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol.

後処理

  1. additionwas added
  2. stirringthe mixture was stirred for 1 hour
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customPurification

出典と根拠

ORDレコード
ord-b9a9d7ccb3224e999e73bdc462941551
出典データセット
uspto-grants-2006_02
特許番号
US06995144B2

関連ノート

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