Methyl iodide → tert-Butyl 4-(2-(benzyl(methyl)amino)ethyl)piperidine-1-carboxylate

HRID 1193335ノート

反応式

HRID 1193335 の反応式
[CH2:1]([NH:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:27]>C1COCC1.CN(C=O)C.O>[CH2:1]([N:8]([CH3:27])[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66799249tert-Butyl 4-(2-(benzylamino)ethyl)piperidine-1-carboxylate

生成物 1

HCID 19261850tert-Butyl 4-(2-(benzyl(methyl)amino)ethyl)piperidine-1-carboxylate収率 34%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

At 0° C., a solution of tert-butyl 4-(2-(benzylamino)ethyl)piperidine-1-carboxylate (400 mg, 1.25 mmol, 1 eq) in THF (10 ml) was added dropwise to a suspension of NaH (110 mg, 2.74 mmol, 1.3 eq, 60% in mineral oil) in DMF (4 ml), and stirring was carried out for 30 min. Then a solution of iodomethane (93 μl, 1.5 mmol, 1.2 eq) in THF (2 ml) was added dropwise at 0° C., and stirring was carried out for 2 h at RT. After monitoring by thin-layer chromatography, the reaction mixture was diluted with water (5 ml) and extracted with ethyl acetate (2×50 ml). The combined organic phases were washed with water and sat. NaCl solution (in each case 50 ml), dried over sodium sulfate and concentrated under reduced pressure. After purification by column chromatography (silica gel, 60% ethyl acetate in hexane), a light-yellow solid was obtained. Yield: 34% (140 mg, 0.42 mmol).

後処理

  1. stirringstirring
  2. waitwas carried out for 2 h at RT
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. washThe combined organic phases were washed with water and sat. NaCl solution (in each case 50 ml),
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customAfter purification by column chromatography (silica gel, 60% ethyl acetate in hexane)
  8. customa light-yellow solid was obtained

出典と根拠

ORDレコード
ord-9c5569e6a9114cfa92547c554fe8cc4c
出典データセット
uspto-grants-2014_03
特許番号
US08680159B2

反応ノート

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