Sodium Hydroxide → HCID 86692463、化合物

HRID 1748514ノート

反応式

HRID 1748514 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH3:16][CH:17]1[C:21](=O)[CH2:20][CH2:19][O:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:14]#[N:15])[CH2:9][CH2:10][N:11]([C@H:21]3[CH2:20][CH2:19][O:18][C@H:17]3[CH3:16])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 18522Dihydro-2-methyl-3(2H)-furanoneHCID 5049666Sodium triacetoxyborohydrideHCID 86692462HCID 86692462、化合物

生成物 1

HCID 86692463HCID 86692463、化合物収率 69.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

To a solution of 4-(5-bromopyridin-2-yl)piperidine-4-carbonitrile (1.15 g) in toluene (14.4 ml), was added 2-methyltetrahydrofuran-3-one (526 mg), and then, sodium triacetoxyborohydride (1.37 g), and the mixture was stirred at room temperature for five hours. Water and 1N aqueous solution of sodium hydroxide were added to the reaction solution at 0° C., and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified with NH silica gel chromatography (n-hexane/ethyl acetate) to give cis-4-(5-bromopyridin-2-yl)-1-(2-methyltetrahydrofuran-3-yl)piperidine-4-carbonitrile (1.05 g) as a yellow solid.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified with NH silica gel chromatography (n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-3fab7abd202c45af8fa18b53f3dd9013
出典データセット
uspto-grants-2015_10
特許番号
US09150555B2

反応ノート

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