Nitration or carboxylation catalysts

An adamantane derivative shown by the following formula (2):

• wherein X1 represents a nitro group, an amino group or N-substituted amino group which may be protected by a protective group, a carboxyl group which may be protected by a protective group, or a hydroxymethyl group which may be protected by a protective group;
• and X3 and X4 may be the same or different from each other, and represents a hydrogen atom, an alkyl group, a nitro group, an amino group or N-substituted amino group which may be protected by a protective group, a carboxyl group which may be protected by a protective group, a hydroxymethyl group which may be protected by a protective group or an isocyanato group;
• (i) when X1 is a nitro group, X2 represents N-amino group which may be protected by a protective group, a hydroxymethyl group which may be protected by a protective group, or an isocyanato group;
• (ii) when X1 is an amino group or N-substituted amino group which may be protected by a protective group, X2 represents an isocyanato group;
• (iii) when X1 is a carboxyl group which may be protected by a protective group, X2 represents a hydroxymethyl group which may be protected by a protective group, or an isocyanato group;
• and
• (iv) when X1 is a hydroxymethyl group which may be protected by a protective group, X2 represents an isocyanato group;
• or a salt thereof.

An adamantane derivative shown by the following formula (3):

• wherein X5 represents a carbamoyl group which may have a substituent, a nitro group, a substituted hydroxycarbonylamino group, or a saturated aliphatic acylamino group or aromatic acylamino group;
• X7 and X8 are the same or different from each other, and represent a hydrogen atom, an alkyl group, a nitro group, an amino or N-substituted amino group which may be protected by a protective group, a carboxyl group which may be protected by a protective group, a hydroxymethyl group which may be protected by a protective group, or an isocyanato group;
• (i) when X5 is a carbamoyl group which may have a substituent, X6 represents a carboxyl group, a substituted hydroxycarbonyl group, or a nitro group;
• (ii) when X5 is a nitro group, X6 represents a substituted hydroxycarbonyl group;
• (iii) when X5 is a substituted hydroxycarbonylamino group, X6 represents a substituted hydroxycarbonyl group, a hydroxymethyl group which may be protected by a protective group, or an amino group which may be protected by a protective group;
• and
• (iv) when X5 is a saturated aliphatic acylamino group or aromatic acylamino group, X6 represents an amino group which may be substituted by an alkyl group;
• or a salt thereof.

A process for producing a diaminoadamantane derivative shown by the following formula (2j):

• wherein X1j and X2j represent an amino group or N-substituted amino group which may be protected by a protective group;
• and X3 and X4 are the same or different from each other, and represent a hydrogen atom, an alkyl group, a nitro group, an amino group or N-substituted amino group which may be protected by a protective group, a carboxyl group which may be protected by a protective group, a hydroxymethyl group which may be protected by a protective group, or an isocyanato group;
• or a salt thereof,
• which comprises the steps of
• contacting a compound shown by the following formula (2h):
• wherein X2h represents a hydrogen atom or a nitro group;
• X3 and X4 are have the same meanings as defined above;
• with a nitrogen oxide, in the presence of an imide compound shown by the following formula (1):
• wherein R1 and R2 are the same or different from each other and represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, and an acyl group;
• R1 and R2 may bond together to form a double bond, or an aromatic or nonaromatic ring;
• Y represents an oxygen atom or a hydroxyl group;
• and n denotes an integer of 1 to 3,
• to produce a dinitroadamantane derivative shown by the following formula (2i):
• wherein X1i and X2i each represents a nitro group;
• and X3 and X4 have the same meanings as defined above;
• and
• reducing said dinitroadamantane derivative shown by the formula (2i) to produce a corresponding diamino compound.