Hydrochloric Acid → 3-(4-Tert-butoxycarbonylaminophenyl)propanol

HRID 1978392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1978392
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([O:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](OCC)=[O:28])=[CH:21][CH:20]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].Cl>O1CCCC1>[C:11]([O:15][C:16]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH2:27][OH:28])=[CH:23][CH:24]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 21994026Ethyl 3-(4-tert-butoxycarbonylaminophenyl)propionate

Produkt 1

HCID 219940133-(4-Tert-butoxycarbonylaminophenyl)propanolAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Diisobutylaluminium hydride(l.5 M in toluene, 30.5 ml, 45.8 mmol) was added dropwise to a stirred solution of ethyl 3-(4-tert-butoxycarbonylaminophenyl)propionate (6.10 g, 20.8 mmol) in tetrahydrofuran (60 ml) at 0° C. and the mixture was stirred at 0° C. for 1 hour. 2N-hydrochloric acid was added to the mixture and the mixture was extracted with ethyl acetate. The extract was successively washed with water, saturated aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (3:2) to give 3-(4-tert-butoxycarbonylaminophenyl)propanol as a colorless oil (2.66 g, 51%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was successively washed with water, saturated aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (3:2)

Quellen und Nachweise

ORD-Eintrag
ord-2707dce753ee478ba7fbac6412c6619f
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235731B1

Notizen zur Reaktion

Wird geladen…