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

HRID 1854678ノート

反応式

HRID 1854678 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 585920724-(N-Boc-N-methylamino)-benzaldehyde収率 79%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-819199a1a72347e79b25217e5e9d37e4
出典データセット
uspto-grants-2015_02
特許番号
US08962674B2

反応ノート

読み込み中…