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

HRID 1193253노트

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HRID 1193253 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7018c89c228d441d9c93f94cf489fd98
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680159B2

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