Reaction #985320

Reaction equation

(2R)-2-(2-Carbazol-9-yl-2-oxo-ethyl)-pentanoic acid benzyl ester

→

sub-title compound

Yield 84.4%

(2R)-2-(2-Carbazol-9-yl-2-oxo-ethyl)-pentanoic acid

Yield 84.4%

Solvents

EtOAc

Conditions

Workup

1. 1
   Filtrationwas filtered through a celite pad
2. 2
   Concentrationconcentrated

Procedure

A stirred solution of (2R)-2-(2-Carbazol-9-yl-2-oxo-ethyl)-pentanoic acid benzyl ester (4.50 g, 11.26 mmol) in EtOAc (60 mL) was treated with 10% Pd on carbon (˜400 mg) and the reaction mixture then placed under an atmosphere of hydrogen. After 1 h further 10% Pd on carbon (˜300 mg) was added and the reaction mixture was placed under hydrogen, with stirring, for a further 3 h after which the reaction mixture was filtered through a celite pad and concentrated to give the sub-title compound (2.94 g, 84%) as a white solid which also contained carbazole: 1H NMR (400 MHz, CDCl3) δ 0.92-1.04 (3H, m), 1.32-2.00 (4H, m), 3.19-3.34 (2H, m), 3.58-3.70 (1H, m), 7.30-7.53 (4H, m), 8.00-8.30 (4H, m).

Source