Reaktion #363056

Reaktionsgleichung

2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

furfural

acetic acid

cyano sodium borohydride

→

5-chloro-2-(furan-2-ylmethyl)amino-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

Ausbeute 98.3%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated, to which
2. 2
   workup.ADDITIONwere added water (30 ml) and ethyl acetate (50 ml)
3. 3
   Extraktionto extraction
4. 4
   WaschenThe organic layer was washed with water
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off
7. 7
   Sonstigethe residue was purified by means of a silica gel column chromatography

Vorschrift

In methanol (15 ml) were dissolved 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.5 g) produced in Example (1) and furfural (0.15 g). To the solution were added acetic acid (0.1 g) and cyano sodium borohydride (0.11 g). The mixture was stirred for 40 minutes at 60° C. The reaction mixture was concentrated, to which were added water (30 ml) and ethyl acetate (50 ml), followed by subjecting the mixture to extraction. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give 5-chloro-2-(furan-2-ylmethyl)amino-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.6 g) as a colorless oily product.

Quelle