Deuterated 3-methanesulfonylpropionitrile
The present invention relates to purified compounds of 3-methanesulfonylpropionitrile, in which at least one of the hydrogen, oxygen, sulfur, and nitrogen atoms is substituted with a respective isotope that includes, but not limited to 2 H (deuterium), 3 H (tritium), 13 C, 14 C, 15 N, 17 O, 18 O, and 35 S. The purified compound has at least 90% purity. Preferred compounds are deuterated 3-methanesulfonylpropionitriles.
1. A compound of 3-methanesulfonylpropionitrile or a pharmaceutically acceptable solvate thereof, in which at least one of the hydrogens is substituted with 2 H (deuterium).
2. The compound according to claim 1 , which is
wherein D represents deuterium.
3. The compound according to claim 2 , which is
4. The compound according to claim 2 , which is
5. The compound according to claim 2 , which is
6. A method for preparing the compound of claim 3 , comprising:
reacting 3-bromopropionitrile with an aqueous solution comprising sodium hydrosulfide (NaSH) to form a thiol,
alkylating the thiol with trideuterated-iodomethane under a basic condition to form a sulfide, and
oxidizing the sulfide with hydrogen peroxide to form the compound of claim 3 .
7. A method for preparing the compound of claim 4 , comprising:
protecting 2-bromoethanol-1,1,2,2-d 4 with a protecting group,
alkylating sodium methylsulfinate with the protected 2-bromoethanol-1,1,2,2-d 4 to form a sulfone,
removing the protected group in the sulfone by an acidic condition,
converting the de-protected sulfone to a tosylate, and
reacting the tosylate with a cyanide ion to produce the compound of claim 4 .
8. A method for preparing the compound of claim 5 , comprising:
protecting 2-bromoethanol-1,1,2,2-d 4 with a protecting group,
reacting the protected 2-bromoethanol-1,1,2,2-d 4 with an aqueous solution comprising sodium hydrosulfide (NaSH) to form a thiol,
alkylating the thiol with trideuterated-iodomethane under a basic condition to form a sulfide,
oxidizing the sulfide with hydrogen peroxide to form a sulfone,
removing the protected group in the sulfone by an acidic condition,
converting the de-protected sulfone to a tosylate, and
reacting the tosylate with a cyanide ion to produce the compound of claim 5 .