Method for producing 2-azaadamantane

A method for producing a 2-azaadamantane formula (1):

• the method comprising cyclizing, in the presence of an acid, a compound of formula (2):
• wherein:
• the cyclizing of the compound of formula (2) forms a compound of formula (3), such that the cyclizing directly forms a N—C bond at a first position and a C—H bond at a second position adjacent to the first position, as follows:
• —X—R2 is —C(═O)—R2, —C(═O)—O—R2 or —SO2—R2;
• R2 is a hydrogen atom, a C1-12 alkyl group optionally substituted by Ra, a C1-12 cycloalkyl group optionally substituted by Ra, a C2-12 haloalkyl group, a benzyl group optionally substituted by Ra, or an aryl group
• optionally substituted by Ra;
• R1 is at least one substituent selected from the group consisting of a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a mercapto group, an amino group, a formyl group, a carboxyl group, a sulfo group, a C1-12 alkyl group, a C3-12 cycloalkyl group, a (C1-12 alkyl)oxy group, a (C3-12 cycloalkyl)oxy group, a (C1-12 alkyl)thio group, a (C3-12 cycloalkyl)thio group, a (C1-12 alkyl)amino group, a (C3-12 cycloalkyl)amino group, a di(C1-6 alkyl)amino group, a di(C3-6 cycloalkyl)amino group, a (C1-12 alkyl)carbonyl group, a C3-12 cycloalkylcarbonyl group, a (C1-12 alkyl)oxycarbonyl group, a (C3-12 cycloalkyl)oxycarbonyl group, a (C1-12 alkyl)thiocarbonyl group, a (C3-12 cycloalkyl)thiocarbonyl group, a (C1-12 alkyl)aminocarbonyl group, a (C3-12 cycloalkyl)aminocarbonyl group, a di(C1-6 alkyl)aminocarbonyl group, a di(C3-6 cycloalkyl)aminocarbonyl group, a (C1-12 alkyl)carbonyloxy group, a (C3-12 cycloalkyl)carbonyloxy group, a (C1-12 alkyl)carbonylthio group, a (C3-12 cycloalkyl)carbonylthio group, a (C1-12 alkyl)carbonylamino group, a (C3-12 cycloalkyl)carbonylamino group, a di{(C1-12 alkyl)carbonyl}amino group, a di{(C3-12 cycloalkyl)carbonyl}amino group, a C1-6 haloalkyl group, a C3-6 halocycloalkyl group, a C2-6 alkenyl group, a C3-6 cycloalkenyl group, a C2-6 haloalkenyl group, a C3-6 halocycloalkenyl group, a C2-6 alkynyl group, a C2-6 haloalkynyl group, a benzyl group optionally substituted by Ra, a benzyloxy group optionally substituted by Ra, a benzylthio group optionally substituted by Ra, a benzylamino group optionally substituted by Ra, a dibenzylamino group optionally substituted by Ra, a benzylcarbonyl group optionally substituted by Ra, a benzyloxycarbonyl group optionally substituted by Ra, a benzylthiocarbonyl group optionally substituted by Ra, a benzylaminocarbonyl group optionally substituted by Ra, a dibenzylaminocarbonyl group optionally substituted by Ra, a benzylcarbonyloxy group optionally substituted by Ra, a benzylcarbonylthio group optionally substituted by Ra, a benzylcarbonylamino group optionally substituted by Ra, a di(benzylcarbonyl)amino group optionally substituted by Ra, an aryl group optionally substituted by Ra, an aryloxy group optionally substituted by Ra, an arylthio group optionally substituted by Ra, an arylamino group optionally substituted by Ra, a diarylamino group optionally substituted by Ra, an arylcarbonyl group optionally substituted by Ra, an aryloxycarbonyl group optionally substituted by Ra, an arylthiocarbonyl group optionally substituted by Ra, an arylaminocarbonyl group optionally substituted by Ra, a diarylaminocarbonyl group optionally substituted by Ra, an arylcarbonyloxy group optionally substituted by Ra, an arylcarbonylthio group optionally substituted by Ra, an arylcarbonylamino group optionally substituted by Ra, and a di(arylcarbonyl)amino group optionally substituted by Ra, and when the number of substituents is two or more, the respective substituents are optionally the same or different;
• and
• Ra is from 1 to 5 substituents selected from the group consisting of a halogen atom, a C1-6 alkyl group, a C1-6 haloalkyl group, a C3-6 cycloalkyl group, a (C1-6 alkyl)oxy group, a (C1-6 alkyl)oxy (C1-6 alkyl) group, a (C1-6 alkyl)sulfenyl (C1-6 alkyl) group, a C1-6 haloalkoxy group, a (C1-6 alkyl)sulfenyl group, a (C1-6 alkyl)sulfinyl group, a (C1-6 alkyl)sulfonyl group, a (C1-6 haloalkyl)sulfenyl group, a (C1-6 haloalkyl)sulfinyl group, a (C1-6 haloalkyl)sulfonyl group, a C2-6 alkenyl group, a C2-6 haloalkenyl group, a (C2-6 alkenyl)oxy group, a (C2-6 haloalkenyl)oxy group, a (C2-6 alkenyl)sulfenyl group, a (C2-6 alkenyl)sulfinyl group, a (C2-6 alkenyl)sulfonyl group, a (C2-6 haloalkenyl)sulfenyl group, a (C2-6 haloalkenyl)sulfinyl group, a (C2-6 haloalkenyl)sulfonyl group, a C2-6 alkynyl group, a C2-6 haloalkynyl group, a (C2-6 alkynyl)oxy group, a (C2-6 haloalkynyl)oxy group, a (C2-6 alkynyl)sulfenyl group, a (C2-6 haloalkynyl)sulfinyl group, a (C2-6 alkynyl)sulfonyl group, a (C2-6 haloalkynyl)phenyl group, a (C2-6 haloalkynyl)sulfinyl group, a (C2-6 haloalkynyl)sulfonyl group, NO2, CN, a formyl group, OH, SH, NH2, SCN, a (C1-6 alkyl)oxycarbonyl group, a (C1-6 alkyl)carbonyl group, a (C1-6 haloalkyl)carbonyl group, a (C1-6 alkyl)carbonyloxy group, a phenyl group, a (C1-6 alkyl)amino group and a di(C1-6 alkyl)amino group, and when the number of substituents is two or more, the respective substituents are optionally the same or different.