L-tartrate of...

Details L-tartrate of... L-tartrate of...

1999-06-29

2001-11-13

Chang, Ceila (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

06316628

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an L-tartrate of a trans-(−)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine compound, and a process for preparing the same. More specifically, the present invention relates to an L-tartrate of a trans-(−)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine compound which is useful as an intermediate for pharmaceuticals such as paroxetine which is useful, for example, as an antidepressant, and a process for preparing the same.
2. Discussion of the Related Art
Conventionally, a salt of tartranilic acid derivative of a trans-(−)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine compound, represented by the formula (III):
wherein R
2
is hydrogen atom, methyl group or benzyl group, has been prepared by optically resolving a trans-(±)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine compound represented by the formula (IV):
wherein R
2
is the same as defined above, with a tartranilic acid derivative, such as (+)-2′-nitrotartranilic acid or (+)-2′-chlorotartranilic acid, as an optically resolving agent.
However, since the tartranilic acid derivative used as an optically resolving agent is extremely expensive, there is a defect in this process that a complicated procedure of collecting the tartranilic acid derivative after its use and purifying it for reuse is necessitated.
In addition, since the salt of tartranilic acid of the resulting trans-(−)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine compound prepared by using the optically resolving agent has a low bulk density of 230 g/l or so, there arises a defect of poor production efficiency.
In view of the above problems, an object of the present invention is to provide a compound capable of being suitably used as an intermediate for pharmaceuticals such as paroxetine which is useful, for example, as an antidepressant, and a process for preparing the compound using an inexpensive optically resolving agent with high production efficiency.
These and other objects of the present invention will be apparent from the following description.
SUMMARY OF THE INVENTION
The present invention pertains to:
[1] an L-tartrate of a trans-(−)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine compound, represented by the formula (I):
wherein R
1
is hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 6 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms; and
[2] a process for preparing a trans-(−)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine compound, represented by the formula (I), comprising reacting a trans-(±)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine compound represented by the formula (II):
wherein R
1
is the same as defined above, with L-tartaric acid.


REFERENCES:
patent: 4007196 (1977-02-01), Christensen et al.
patent: 5948914 (1999-09-01), Sugi et al.
patent: 0223334A1 (1987-05-01), None
patent: 0802185A1 (1997-10-01), None
patent: 0812827A1 (1997-12-01), None
patent: 9403428 (1994-02-01), None
Montzka et al. “Substituted tartranilic acids . . . ” J. Org. chem. v. 33, p. 3993-5, 1968.*
Jacques et al. “Enantiomers, racemates and resolutions” Krieger Pub. p. 259-260, 1994.*
Nass et al. “Rational solvent selection for cooling crystallizations” CA 120:326130 (1994).
Rico et al. “N-methylsydnone a new solvent for molecular aggregation” CA 119:434789 (1992).
Pavia et al. “Introduction to organic laboratory techniques . . . ” Saunders Publ. p. 481-489, 1988.*
Heterocyles, 109:6427k, p. 609 (1988).
English language abstract of JP-A-9-278754.

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