Hydrochloric Acid → (4S)-4-Cyclohexyl-L-proline--hydrogen chloride (1/1)

Participants

Reaction Steps

A slurry of (trans)-4-phenyl-L-proline (50 g, 0.262 moles) and platinum oxide (10 g) in absolute ethanol (1200 ml) was treated with 5.62 N ethanolic HCl (46.5 ml, 0.261 moles) and shaken until all the solid had gone into solution. The solution was then purged with argon and hydrogenated on a Parr apparatus at 50 psi overnight. After this time, the untake of hydrogen had ceased and NMR indicated complete reduction. The reaction mixture was filtered through a pad of Cellite and concentrated in vacuo. The residue was triturated with diethylether and filtered to yield 60.0 g of (trans)-4-cyclohexyl-L-proline hydrochloride as snow white crystals, m.p. 170°-171° C.

Provenance & Evidence