Methyl iodide → Methyl (R)-3-((tert-butoxycarbonyl)(methyl)amino)-2,3-dihydro-1H-indene-5-carboxylate

HRID 1193253ノート

反応式

HRID 1193253 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:24]I.[Cl-].[NH4+]>CN(C=O)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH3:24])[C@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59505324Methyl (R)-3-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-5-carboxylate

生成物 1

HCID 59505713Methyl (R)-3-((tert-butoxycarbonyl)(methyl)amino)-2,3-dihydro-1H-indene-5-carboxylate収率 95%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of (R)-methyl 3-(tert-butoxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate (stage (ii) A-07) (60 g, 20.62 mmol, 1.0 eq.) in DMF (20 ml) was added dropwise at 0° C. to a suspension of NaH (1.24 g, 30.93 mmol, 1.5 eq., 60% in mineral oil) in DCM (20 ml) and stirring was carried out for 30 minutes. Methyl iodide (2.6 ml, 41.24 mmol, 2.0 eq.) was then added at 0° C. and stirring was carried out for 3 hours at RT. After monitoring by TLC, sat. ammonium chloride solution (200 ml) was added and extraction with ethyl acetate (3×250 ml) was carried out. The combined org. phases were washed with water and sat. NaCl solution (in each case 400 ml), dried over sodium sulfate, concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate in hexane). Yield: 95% (6.0 g, 19.67 mmol).

後処理

  1. stirringstirring
  2. waitwas carried out for 3 hours at RT
  3. additionwas added
  4. extractionextraction with ethyl acetate (3×250 ml)
  5. washphases were washed with water and sat. NaCl solution (in each case 400 ml),
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography (silica gel, 10% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-7018c89c228d441d9c93f94cf489fd98
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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