Patent ID: 7495122

Claim:
A process for producing a compound represented by a formula [1]: wherein R 1 and R 2 respectively represent a light or heavy hydrogen atom, R 3 represents a light or heavy hydrogen atom or a methyl group in which three hydrogen atoms are respectively light or heavy hydrogen atoms, and R 4 is a norbornyl group provided that four or more hydrogen atoms in the norbornyl group are heavy hydrogen atoms, comprising: (i) reacting a norborneol with heavy water in the presence of palladium catalyst under an atmosphere of light hydrogen gas, or (ii) reacting a norbornanone with heavy water in the presence of palladium catalyst under an atmosphere of light hydrogen gas and then reducing the obtained deuterated norbornanone, thereby to obtain a deuterated norborneol containing four or more heavy hydrogen atoms in its norbornyl group; and reacting said deuterated norborneol with a compound represented by a formula [2]: wherein R 1 and R 2 respectively represent a light or heavy hydrogen atom, R 3 represents a light or heavy hydrogen atom or a methyl group in which three hydrogen atoms are respectively light or heavy hydrogen atoms, and X represents a halogen atom, a hydroxyl group or an alkoxy group.