Intermediate compound for synthesizing pharmaceutical agent and production method thereof

A production method of an optically active compound represented by the formula (I),

• wherein R is an aryl optionally having substituent(s) or a heteroaryl optionally having substituent(s), and a carbon atom marked with * is an asymmetric carbon atom;
• which comprises Step (1) or (2):
• Step (1) synthesizing an optically active compound represented by the formula 5, which comprises the following steps:
• wherein R is an aryl optionally having substituent(s) or a heteroaryl optionally having substituent(s), X1 is a halogen, and R1 is a C1-C6 alkyl, an aralkyl optionally having substituent(s) or a C2-C6 alkenyl
• reacting a compound of the formula 1 with a borane or a complex thereof in a solvent in the presence of (S)-2-methyl-CBS-oxazaborolidine to give a compound of the formula 2,
• reacting the compound of the formula 2 with a base in a solvent to give a compound of the formula 3, and
• reacting the compound of the formula 3 with an amine of the formula 4 to give the compound of the formula 5;
• or
• Step (2) synthesizing an optically active compound represented by the formula 25, which comprises the following steps:
• wherein R is an aryl optionally having substituent(s) or a heteroaryl optionally having substituent(s), X1 is a halogen, and R1 is a C1-C6 alkyl, an aralkyl optionally having substituent(s) or a C2-C6 alkenyl;
• reacting a compound of the formula 21 with a borane or a complex thereof in a solvent in the presence of (R)-2-methyl-CBS-oxazaborolidine to give a compound of the formula 22,
• reacting the compound of the formula 22 with a base in a solvent to give a compound of the formula 23, and
• reacting the compound of the formula 23 with an amine of the formula 24 to give the compound of the formula 25.