Acetic Acid → tert-Butyl 4-(1-(4-aminonaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate

HRID 2069061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069061
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:19]=2)[CH3:17])=[CH:6][CH:5]=1)([O-])=O.CC(O)=O.CCOC(C)=O.[H][H]>CO.[Pt]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:19]=2)[CH3:17])=[CH:6][CH:5]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 58532579tert-Butyl 4-(1-(4-nitronaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 58532582tert-Butyl 4-(1-(4-aminonaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamateAusbeute 107,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of the nitroarene (54) (0.61 g, 1.441 mmol) in a mixture of MeOH (20.0 mL), AcOH (5.0 mL) and EtOAc (10.0 mL) was passed through a Thales H-Cube (1.0 mL·min−1, 45° C., 55 mm, 10% Pt/C Cat-Cart, full hydrogen mode). The solvent was evaporated in vacuo and the residue was partitioned between saturated aqueous NaHCO3 solution and EtOAc. The organic layer was washed with water and brine and then dried (MgSO4) and evaporated in vacuo to furnish the title compound (55) (0.61 g, 97%): m/z 394 (M+H)+ (ES+).

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between saturated aqueous NaHCO3 solution and EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e0487f5068474bd182e0553a7081f50e
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299073B2

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