Water → Benzyl 4-methoxypiperidine-1-carboxylate

HRID 253060

反応式

HRID 253060 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:20]I.O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH3:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

生成物 1

HCID 23024301Benzyl 4-methoxypiperidine-1-carboxylate収率 45%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1-benzyloxycarbonyl-4-hydroxypiperidine (1.3 g) in dimethylformamide (10 mL) was added sodium hydride (360 mL) under ice cooling and the mixture was stirred at room temperature under nitrogen-gas atmosphere for 1 hours. To the reaction mixture was added methyl iodide (374 μL) under ice-cooling and the mixture was stirred at the same temperature for 1 hour and at room temperature for 2 hours. To the reaction mixture was added water and ethyl acetate and the mixture was stirred. The organic layer washed with a brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=88/12 to 70/30) to obtain 1-benzyloxycarbonyl-4-methoxypiperidine (622 mg, yield: 45%) as a pale yellow oil.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 1 hour and at room temperature for 2 hours
  3. stirringthe mixture was stirred
  4. washThe organic layer washed with a brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=88/12 to 70/30)

出典と根拠

ORDレコード
ord-e9dd1c0189ef49e99991622f5a437a99
出典データセット
uspto-grants-2011_01
特許番号
US07872006B2

関連ノート

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