3,4-dihydro-2H-pyran → 2-Tetrahydropyranyl 4-benzyloxycarbonylaminobicyclo[2,2,2]octane-1-carboxylate

HRID 227931ノート

反応式

HRID 227931 の反応式
[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([OH:22])=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([O:22][CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][O:23]3)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 106622014-(Benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylic acid

生成物 1

HCID 231496802-Tetrahydropyranyl 4-benzyloxycarbonylaminobicyclo[2,2,2]octane-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-Benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylic acid (1.00 g) was dissolved in dichloromethane (10 mL). To this solution, 3,4-dihydro-2H-pyran (1.20 mL) and p-toluenesulfonic monohydrate (6.3 mg) were sequentially added and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was sequentially washed with a saturated aqueous solution of sodium bicarbonate and saturated brine. The mixture was then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant:hexane:ethyl acetate=4:1) to give 2-tetrahydropyranyl 4-benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylate (1.18 g).

後処理

  1. washThe reaction mixture was sequentially washed with a saturated aqueous solution of sodium bicarbonate and saturated brine
  2. dry with materialThe mixture was then dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluant:hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-9caf53b1ef1a44058c53fc4c9fa6d93c
出典データセット
uspto-grants-2009_07
特許番号
US07560569B2

反応ノート

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