Formaldehyde → 4-hydroxy-N-methylproline

Participants

Reaction Steps

A suspension of 10% palladium on carbon in water (25 ml) was added to a suspension of trans-4-hydroxy-L-proline (6.576 g., 50.10 mmol) in methanol (100 ml) and 37% aqueous formaldehyde (16 ml, 213.5 mmol) in a Parr bottle. The bottle was pressurized to 50 psi with hydrogen and shaken overnight. The catalyst was removed by filtration through a pad of celite which was washed thoroughly with methanol (100 ml). Evaporation of the methanol and excess formaldehyde yielded N-methyl-trans-4-hydroxy-L-proline as a white solid which was recrystallized from methanol/diethyl ether to give 6.425 g. of white needles, m.p. 236°-238 ° (decomposition with gas evolution).

Provenance & Evidence