반응 #56659

반응 방정식

Naphthalene-1-carboxylic acid

→

(Naphthalene-1-yl)-methanol

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITION5 equiv. of borane dimethylsulfide complex are added
2. 2
   기타The mixture obtained
3. 3
   workup.ADDITIONdiluted with EtAc
4. 4
   세척washed with 1N HCl and 5% NaHCO3 solution
5. 5
   기타dried
6. 6
   기타solvent is evaporated

실험 절차

Naphthalene-1-carboxylic acid is dissolved in dry THF and 5 equiv. of borane dimethylsulfide complex are added. The mixture obtained is stirred at rt, diluted with EtAc, washed with 1N HCl and 5% NaHCO3 solution, dried and solvent is evaporated. (Naphthalene-1-yl)-methanol is obtained, which is dissolved in CH2Cl2. To the solution obtained 1.5 equiv. of Dess-Martin reagent are added at rt. The mixture obtained is diluted with EtAc, extracted with 1N HCl and 5% NaHCO3-solution, dried and solvent is evaporated. Naphthalene-1-carboxaldehyde is obtained and dissolved with 1 equiv. of racemic-Boc-α-phosphonoglycine trimethylester in CH2Cl2 and 1.1 equiv. of DBU are added. The mixture obtained is stirred at rt and treated in sequence with 1N HCl and 5% NaHCO3 solution. The phases obtained are separated, the organic phase obtained is dried and solvent is evaporated. 2-Boc-amino-3-(naphthalene-1-yl)-acrylic acid methyl ester (cis/trans mixture) is obtained, is dissolved in MeOH/H2O at pH 6.5 (phosphate buffer) and 20 w/w % of 10% Pd/C are added. The mixture obtained is hydrogenated at rt and 50 bar, the catalyst is filtered off and from the filtrate obtained solvent is evaporated. Racemic naphythylalanine methylester is obtained, dissolved in methanolic NH3 and stirred. The mixture obtained is subjected to extractive work up. Racemic naphythylalanine amide is obtained.

출처