Reaction #1458441

Reaction equation

diisobutylaluminum hydride

N-Cyclohexanoylphenylalanine methyl ester

→

N-cyclohexanoylphenylalanine Aldehyde

Solvents

toluene

ethylene glycol dimethyl ether

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   OtherThe reaction is quenched by dropwise addition of 2N hydrochloric acid
3. 3
   ExtractionThe mixture is extracted with cold ethyl acetate
4. 4
   WashThe ethyl acetate solution is washed with brine
5. 5
   Dryingdried over sodium sulfate
6. 6
   ConcentrationConcentration in vacuo
7. 7
   Otherfurnishes a white solid, which
8. 8
   Otheris purified by silica gel chromatography

Procedure

N-Cyclohexanoylphenylalanine methyl ester (0.5 g) is dissolved in ethylene glycol dimethyl ether (20 mL). The solution is cooled to 70° C. and diisobutylaluminum hydride (2.04 mL of a 1.5M solution in toluene) is added. The resulting reaction mixture is stirred at −70° C. for 2 hours. The reaction is quenched by dropwise addition of 2N hydrochloric acid. The mixture is extracted with cold ethyl acetate. The ethyl acetate solution is washed with brine and dried over sodium sulfate. Concentration in vacuo furnishes a white solid, which is purified by silica gel chromatography. 1H NMR (300 MHz, DMSO-d6): 9.5 (s, 1H), 8.2 (d, 1H), 7.2 (m, 5H), 4.2 (m, 1H), 3.2 (d, 1H), 2.7 (d, 1H), 2.1 (m, 1H), 1.6 (br.m, 4H), 1.2 (br.m, 6H). R (KBr): 3300, 3050, 2900, 2850, 2800, 1700, 1600, 1500 cm-1.

Source