Acetic Acid → (2S)-2-(((tert-butoxy)carbonyl)amino)-3-cyclohexylpropanoic acid

Participants

Reaction Steps

Platinum oxide catalyst (5 g) is added to a solution of N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine (120 g, 0.452 mole) in absolute ethanol (1 l). The mixture is placed on a Parr reduction apparatus at 50 lb. pressure. The absorption of hydrogen is rapid and the hydrogen reservoir needs continued refilling. The reduction proceeds overnight and after 20 hours is completed. The mixture is filtered through Celite and concentrated in vacuo to give 124.4 g of the title F compound as a glassy solid colorless residue; [α]D =-9.5° (c=1, methanol). TLC (silica gel; toluene:acetic acid, 4:1) Rf =0.62.

Provenance & Evidence