4'-Fluorobiphenyl-4-carbaldehyde → tert-Butyl 3-(((4'-fluorobiphenyl-4-yl)methylamino)methyl)benzylcarbamate

HRID 1889677ノート

反応式

HRID 1889677 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH2:16][CH2:17][C:18]1[CH:19]=[C:20]([CH:30]=[CH:31][CH:32]=1)[CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][NH:16][CH2:17][C:18]3[CH:19]=[C:20]([CH:30]=[CH:31][CH:32]=3)[CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 13925504'-Fluorobiphenyl-4-carbaldehydeHCID 2756043tert-butyl N-((3-(aminomethyl)phenyl)methyl)carbamateHCID 4311764Sodium borohydride

生成物 1

HCID 58531402tert-Butyl 3-(((4'-fluorobiphenyl-4-yl)methylamino)methyl)benzylcarbamate収率 85.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

4′-Fluorobiphenyl-4-carbaldehyde (1.0 g, 5 mmol, 1.0 eq) and tert-butyl 3-(amino methyl)benzylcarbamate (1.18 g, 5 mmol, 1 eq) were dissolved in dry methanol under nitrogen and refluxed for 4 h. The reaction mass was cooled to 0° C. and sodium borohydride (570 mg, 15 mmol, 3 eq) was added portionwise at 0° C. over 20-30 minutes. The mixture was stirred for 1 h at 0° C. and then the reaction was quenched with 10% aq. sodium bicarbonate solution. The mixture was stirred at room temperature for 1 h. The resulting solution was completely evaporated under vacuum and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by silica gel (60-120) column chromatography using 5-10% methanol dichloromethane as the eluent to afford the desired compound (1.8 g, 85%) as a light yellow liquid. 1H NMR (400 MHz, DMSO-d6) δ 1.30-1.37 (d, 9H), 3.66-3.69 (d, 4H), 4.09-4.11 (d, 2H), 7.07-7.09 (d, 1H), 7.18-7.29 (m, 6H), 7.36-7.42 (m, 1H), 7.56-7.59 (m, 2H), 7.65-7.67 (d, 2H), 7.68-7.70 (m, 2H). MS (ESI): 421.0 (M+H)+.

後処理

  1. temperaturerefluxed for 4 h
  2. customthe reaction was quenched with 10% aq. sodium bicarbonate solution
  3. stirringThe mixture was stirred at room temperature for 1 h
  4. customThe resulting solution was completely evaporated under vacuum
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel (60-120) column chromatography

出典と根拠

ORDレコード
ord-ce66057c56d54259a7e15870cd1590fe
出典データセット
uspto-grants-2013_08
特許番号
US08501992B2

反応ノート

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