(Dimethyl sulfide)trihydroboron → tert-butyl N-[1-[3-(hydroxymethyl)phenyl]ethyl]carbamate

HRID 467503ノート

反応式

HRID 467503 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](O)=[O:15])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.CSC>C1COCC1>[OH:15][CH2:14][C:13]1[CH:12]=[C:11]([CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:10])[CH:19]=[CH:18][CH:17]=1

参加物

4

反応物 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 223270393-(1-((tert-Butoxycarbonyl)amino)ethyl)benzoic acid

生成物 1

HCID 58070261tert-butyl N-[1-[3-(hydroxymethyl)phenyl]ethyl]carbamate収率 68.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

3-[1-(tert-Butoxycarbonylamino)ethyl]benzoic acid (7.57 g, 28.53 mmol) was dissolved in anhydrous THF (45 mL) and 2M borane-dimethylsulfide in THF (42.8 mL, 85.6 mmol) was added dropwise at ambient temperature. The reaction was stirred at this temperature for 3 hours then cooled to 0° C. and quenched with MeOH. The solvents were removed under reduced pressure and the resulting residue partitioned between 1M HCl and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate (×1) and brine (×1), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™ eluting with 0 to 30% EtOAc/petroleum ether) to give the sub-title compound as a white solid (4.91 g, 68% Yield). 1H NMR (400 MHz, DMSO) δ 1.28 (d, 3H), 1.36 (s, 9H), 4.47 (d, 2H), 4.54-4.64 (m, 1H), 5.17 (t, 1H), 7.14 (d, 2H), 7.23 (d, 2H) and 7.38 (d, 1H) ppm; MS (ES+) 252.3.

後処理

  1. customquenched with MeOH
  2. customThe solvents were removed under reduced pressure
  3. customthe resulting residue partitioned between 1M HCl and ethyl acetate
  4. washThe organic layer was washed with saturated sodium bicarbonate (×1) and brine (×1)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (ISCO Companion™ eluting with 0 to 30% EtOAc/petroleum ether)

出典と根拠

ORDレコード
ord-1e359becd0b1414788764079aa424676
出典データセット
uspto-grants-2014_01
特許番号
US08623869B2

反応ノート

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