Process for production of aralkyloxypyrrolidine derivative

Details Process for production of aralkyloxypyrrolidine derivative Process for production of aralkyloxypyrrolidine derivative

2011-07-05

2011-07-05

Nolan, Jason M (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

07973176

ABSTRACT:
The present invention provides a process for producing a 3-aralkyloxypyrrolidine derivative which is important for production of pharmaceutical products and the like. In the present invention, a N-protected-3-hydroxypyrrolidine is converted into a N-protected-3-aralkyloxypyrrolidine by allowing an aralkyl halide to act in the presence of a base and at least one of a metal halide and a phase-transfer catalyst followed by deprotecting a N-protecting group to convert it to a 3-aralkyloxypyrrolidine derivative and subsequently treating the derivative in a solvent containing a polar solvent, thereby obtaining the 3-aralkyloxypyrrolidine derivative as a crystal. According to the present invention, a 3-aralkyloxypyrrolidine derivative of high purity can be produced conveniently and efficiently on an industrial scale.

REFERENCES:
patent: 5037841 (1991-08-01), Schohe et al.
patent: 5854268 (1998-12-01), Baker et al.
patent: 7268236 (2007-09-01), Kano et al.
patent: 1-311059 (1989-12-01), None
patent: 96/04274 (1996-02-01), None
patent: 03/082815 (2003-10-01), None
patent: WO 2004099137 (2004-11-01), None
Pavia et al., Introduction to Organic Laboratory Techniques—A Microscale Approach 1990, Technique 5 on pp. 577-596.
N.G. Anderson, Practical Process Research & Development 2000, Chapter 10, pp. 203-221.
Extended European Search Report issued for the counterpart European Patent Application No. 06 79 6649 on Apr. 24, 2009.
International Search Report issued Nov. 21, 2006 in the International (PCT) Application PCT/JP2006/316435 of which the present application is the U.S. National Stage.
International Preliminary Report on Patentability issued Mar. 6, 2008 in the International (PCT) Application PCT/JP2006/316435 of which the present application is the U.S. National Stage together with translation of PCT Written Opinion issued for the International Application.
Francine Sternfeld et al., “Synthesis and Serotonergic Activity of 3-[2-(Pyrrolidin-1-yl)ethyl]indoles: Potent Agonists for the h5-HT1DReceptor with High Selectivity over the h5-HT1BReceptor”, Journal of Medicinal Chemistry, vol. 42, No. 4, pp. 677-690, 1999.
Zhenliang Chen et al., “Cumyl: A Better N-Protecting Group of α-Diazo Acetamides for Intramolecular C-H Insertion Reaction and its Application in the Synthesis of Pregabalin and 3-Benzyloxy Pyrrolidine”, Synlett, No. 10, pp. 1763-1764, 2004.
Shigeru Arai et al., “Phase-transfer-catalyzed asymmetric Michael reaction using newly-prepared chiral quaternary ammonium salts derived from L-tartrate”, Tetrahedron Letters, vol. 43, No. 52, pp. 9535-9537, 2002.
Dominique Potin et al., “De novo design, synthesis, and in vitro activity of LFA-1 antagonists based on a bicyclic[5.5]hydantoin scaffold”, Bioorganic & Medicinal Chemistry Letters, vol. 15, No. 4, pp. 1161-1164, 2005.
Armen M. Boldi et al., “Solid-Phase Library Synthesis of Alkoxyprolines”, Journal of Combinatorial Chemistry, vol. 3, No. 4, pp. 367-373, 2001.
Frank Schieweck et al., “Synthesis of geminal bis(hydroxymethyl)pyrrolidine and pyrrolizidine imino sugars”, Journal of the Chemical Society, Perkin Transactions, vol. 24, pp. 3409-3414, 2001.
Notice of Reasons for Refusal, and English translation thereof, issued Apr. 22, 2008 in connection with Japanese Patent Application No. JP2007-532139.
Shadan Houjin Nihon Kagakukai Hen (The Chemical Society of Japan ed.), “4.3.1a., Saikessho (Recrystallization)”, Jikken Kagaku Kouza 1 (Experimental Chemical Course 1), vol. 4, pp. 184-186, 1990 along with English translation thereof.

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