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

HRID 467503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 467503
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 58070261tert-butyl N-[1-[3-(hydroxymethyl)phenyl]ethyl]carbamateAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-1e359becd0b1414788764079aa424676
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623869B2

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