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

HRID 467503노트

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HRID 467503 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1e359becd0b1414788764079aa424676
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623869B2

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