Patent ID: 6833468
Filing Date: 2004-12-21
Classification: C07B,C07C

Abstract:
A process for producing an optically active perfluoroalkylcarbinol derivative represented by the formula [1a] or [1b], said process comprising the steps of:(a) reacting an optically active imine represented by the formula [2] with a compound represented by the formula [3], said compound being a hemiacetal of a perfluoroalkylaldehyde or a hydrate of a perfluoroalkylaldehyde, thereby obtaining a condensate between said optically active imine and said compound; and (b) hydrolyzing said condensate under an acid condition, thereby producing said optically active perfluoroalkylcarbinol derivative; wherein the formulas [1a] and [1b] are defined as where R in the formulas [1a] and [1b] is a C1-6 aliphatic alkyl group, a C3-8 cyclic alkyl group, an aryl group, or a heterocyclic group containing nitrogen or sulfur as a hetero atom; and R1 in the formula [1a] is a C1-6 aliphatic alkyl group, a C3-8 cyclic alkyl group, a C1-6 aliphatic alkoxy group, a C3-8 cyclic alkoxy group, an aryl group, or a heterocyclic group containing nitrogen or sulfur as a hetero atom; or a combination of R and R1 in the formula [1a] optionally forms (1) at C4-8 cyclic alkyl group, (2) a four to eight-membered heterocyclic group containing one or two nitrogen or sulfur atoms as hetero atoms, or (3) a condensed ring comprising first and second rings fused together, said first ring being said C4-8 cyclic alkyl group or said four to eight-membered heterocyclic group, said second ring being an aryl group or a heterocyclic group containing nitrogen or sulfur as a hetero atom; Rf in the formulas [1a] or [1b] represents a perfluoroalkyl group; and the symbol * represents an asymmetric carbon; wherein formula [2] is defined as where R, a combination of R and R1, and the symbol * are defined as above; R1 is a hydrogen, a C1-6 aliphatic alkyl group, a C3-8 cyclic alkyl group, a C1-6 aliphatic alkoxy group, a C3-8 cyclic alkoxy group, an aryl group, or a heterocyclic group containing nitrogen or sulfur as a hetero atom; each of R2 and R3 is independently a C1-6 aliphatic alkyl group, a C3-8 cyclic alkyl group, an aryl group, a heterocyclic group containing nitrogen or sulfur as a hetero atom, an alkoxycarbonyl group or a hydroxyalkyl group; and R2 and R3 are not the same substituted groups at the same time; and wherein formula [3] is defined as where R4 is a hydrogen, a C1-6 aliphatic alkyl group, a C3-8 cyclic alkyl group, an aryl group, or a heterocyclic group containing nitrogen or sulfur as a hetero atom; and Rf is defined as above.