Hydrochloric Acid → tert-butyl N-(3-(3-hydroxypropyl)phenyl)carbamate

HRID 1978396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1978396
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([O:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]([CH2:25][CH2:26][C:27](OCC)=[O:28])[CH:22]=[CH:23][CH:24]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].Cl>O1CCCC1>[C:11]([O:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]([CH2:25][CH2:26][CH2:27][OH:28])[CH:22]=[CH:23][CH:24]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 21994062Ethyl 3-(3-tert-butoxycarbonylaminophenyl)propionate

Produkt 1

HCID 21993723tert-butyl N-(3-(3-hydroxypropyl)phenyl)carbamateAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diisobutylaluminium hydride (1.5 M in toluene, 57.0 ml, 85.5 mmol) was added dropwise to a stirred solution of ethyl 3-(3-tert-butoxycarbonylaminophenyl)propionate (9.35 g, 31.9 mmol) in tetrahydrofuran (100 ml) at 0° C. and the mixture was stirred at room temperature for 24 hours. 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 (2:1) to give 3-(3-tert-butoxycarbonylaminophenyl)propanol as a colorless oil (3.24 g, 40%).

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 (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-a7680fa71dee469eaa7ce71a5aa4a2e4
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235731B1

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