Methyl iodide → 4-(N-Boc-N-methylamino)-benzaldehyde

HRID 1854678노트

반응식

HRID 1854678 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:19]I>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([C:9]1[CH:10]=[CH:11][C:12]([CH:13]=[O:14])=[CH:15][CH:16]=1)[CH3:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2771821tert-Butyl (4-formylphenyl)carbamate

생성물 1

HCID 585920724-(N-Boc-N-methylamino)-benzaldehyde수율 79%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-(tert-butoxycarbonylamino)benzaldehyde (250 mg, 1.13 mmol, synthesized at Example 278 (1)) in 2.3 mL of dry N,N-dimethylformamide was added sodium hydride (59 mg, 55%, 1.4 mmol) under nitrogen at 0° C. After the reaction mixture was stirred at room temperature for 30 min, methyl iodide (105 μL, 1.69 mmol) was added with additional stirring overnight. After quench with saturated NH4Cl aqueous solution, the mixture was extracted with diethyl ether. The extract was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40) to obtain the title compound (210 mg, 79%).

후처리

  1. customat 0° C
  2. stirringwith additional stirring overnight
  3. customAfter quench with saturated NH4Cl aqueous solution
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe extract was washed with saturated NaHCO3 aqueous solution, brine
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40)

출처 및 근거

ORD 기록
ord-819199a1a72347e79b25217e5e9d37e4
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962674B2

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