Isopropanol → tert-Butyl ((1R,2S)-1-hydroxy-1-(3-methoxyphenyl)propan-2-yl)carbamate

HRID 1098775

Reaktionsgleichung

Reaktionsgleichung von HRID 1098775
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=[O:20])[C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])[CH:6]=[CH:7][CH:8]=1.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].CC(O)C>C1(C)C=CC=CC=1>[OH:20][C@H:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:16])[CH3:17])[CH3:11]

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 11143Aluminum isopropoxideHCID 59339682tert-Butyl [(1S)-2-(3-methoxyphenyl)-1-methyl-2-oxoethyl]carbamate

Produkt 1

HCID 59339845tert-Butyl ((1R,2S)-1-hydroxy-1-(3-methoxyphenyl)propan-2-yl)carbamateAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of tert-butyl [(1S)-2-(3-methoxyphenyl)-1-methyl-2-oxoethyl]carbamate (13.6 g, 48.7 mmol), aluminum isopropoxide (1.99 g, 9.70 mmol), 2-propanol (41 mL, 535 mmol) in toluene (63 mL) was stirred under an atmosphere of argon at 50° C. overnight. LC/MS showed complete conversion into the alcohol. The mixture was partitioned between ethyl acetate (200 mL) and hydrochloric acid (1M, 200 mL). The organic phase was washed with water (200 mL), dried over magnesium sulfate and concentrated to give the subtitle compound as a syrup (13.5 g). The compound was used in the next step without further purification.

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate (200 mL) and hydrochloric acid (1M, 200 mL)
  2. washThe organic phase was washed with water (200 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2b43d01dd3054975bff97961cfaa410d
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143290B2

Verknüpfte Notizen

Wird geladen…