PROCESS FOR MAKING 2-NITRO-1-ETHANOL DERIVATIVES
A process for making a 2-nitro-1-ethanol derivative of formula III: wherein R3 is as described herein is provided. Novel 2-nitro-1-ethanol derivatives provided.
1 . A process for making a 2-nitroethanol derivative, the process comprising:
(a) providing a compound of formula I:
wherein R is H or CH 2 OH, and R 1 and R 2 are independently H, C 1 -C 6 alkyl, halo substituted C 1 -C 6 alkyl, aryl, or furanyl;
(b) converting the compound of formula I to a compound of formula II:
wherein R 3 is the residue of an alpha carbon reactant or R 3 is —CH 2 -R 4 wherein R 4 is the residue of an alcohol group reactant;
(c) converting the compound of formula II to a 2-nitroethanol derivative of formula III:
2 . The process of claim 1 wherein R is CH 2 OH and the compound of formula I is prepared by reacting tris(hydroxymethyl)nitromethane with a blocking group precursor.
3 . The process of claim 1 wherein R is H and the compound of formula I is prepared by reacting tris(hydroxymethyl)nitromethane with a blocking group precursor followed by treatment with base to remove a —CH 2 OH group.
4 . The process of claim 2 wherein the blocking group precursor is a geminal diether compound, an aldehyde compound, or a ketone compound.
5 . A compound of formula III-1:
wherein R 5 is C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, aryl, or aralkyl-, wherein cycloalkyl and aryl are optionally substituted with 1 or 2 of C 1 -C 6 alkyl, nitro, halo, alkoxy, or carbonyl.
6 . A compound of formula III-2:
wherein R 6 and R 7 are independently H, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, aryl, or aralkyl-, wherein cycloalkyl and aryl are optionally substituted with 1 or 2 of C 1 -C 6 alkyl, nitro, halo, alkoxy, or carbonyl.
7 - 8 . (canceled)