9-cyanononanoic acid → 10-Aminodecanoic acid

A slurry of 9-cyanopelargonic acid (8.6 g, 48 mrnol), a catalytic amount 5%Rh/Al2O3, and 200 mL of 2.0N NH3 -EtOH was shaken under 50 psig of H2 pressure for 6 h, then filtered through dicalite. The filter pad was washed with 100 mL of hot 1:1 MeOH--H2O, and the combined filtrates were concentrated to give 6.1 g of 10-aminodecanoic acid. The crude product (5.7 g) was dissolved in 15.5 mL of 2N NaOH and treated simultaneously with 23 mL of 2N NaOH and 5.8 g of carbobenzoxychloride at 0° C. with vigorous stirring over 0.5 h. Water and 2N NaOH were added as needed to maintain stirring and a pH between 10-14. After stirring for 2.5 h, the reaction was diluted with 400 mL of H2O and filtered through dicalite. The filtrate was acidified (pH 2) with H2SO4, then extracted with ether. The combined ether extracts were dried (Na2SO4), filtered and concentrated. The residue was dissolved in CH3CN, filtered, and the filtrate concentrated to afford 5.3 g of 10-(N-carbobenzoxy)-aminodecanoic acid which was used without further purification: FAB-MS m/z 322 (MH+).

1. filtrationfiltered through dicalite
2. washThe filter pad was washed with 100 mL of hot 1:1 MeOH
3. concentrationH2O, and the combined filtrates were concentrated

ORD record

ord-1b94e4819e824785b7282815d314c2ff

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05888971