Claims
- 1. A method of producing a sulfonic acid ester derivative represented by the general formula (4): wherein n is 2, A represents a phenyl group, which may be substituted, B and B′ are the same or different and each represents a phenyl group, which may be substituted, a straight or branched alkyl group containing 1 to 4 carbon atoms or a hydrogen atom, D represents a straight or branched alkyl group containing 1 to 8 carbon atoms, which may be substituted, or a hydrogen atom and R represents a methanesulfonyl, ethanesulfonyl, p-toluenesulfonyl or p-nitrobenzenesulfonyl group,which comprises reacting an amino alcohol derivative represented by the general formula (1): wherein n, A, B, B′ and D are as defined above, with an organic sulfonyl halide represented by the general formula (3): R—X wherein R is as defined above and X represents a chlorine, bromine or iodine atom, in a mixed solvent composed of an aprotic organic solvent and water in the presence of a non-water-prohibiting inorganic base.
- 2. The production method according to claim 1,wherein the aprotic organic solvent phase and the aqueous phase containing the non-water-prohibiting inorganic base form a two-phase system.
- 3. The production method according to claim 1,wherein the amino alcohol derivative represented by the general formula (1) is in an optically active form and the sulfonic acid ester derivative represented by the general formula (4) is in an optically active form.
- 4. The production method according to claim 1,wherein the aprotic organic solvent is toluene.
- 5. The production method according to claim 1,wherein the non-water-prohibiting inorganic base comprises at least one species selected from the group consisting of lithium hydroxide, sodium hydroxide, potassium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate.
- 6. The production method according to claim 5,wherein the non-water-prohibiting inorganic base comprises at least one species selected from among sodium hydroxide and potassium hydroxide.
- 7. The production method according to claim 1,wherein the organic sulfonyl halide represented by the general formula (3) is methanesulfonyl chloride.
- 8. The production method according to claim 1,wherein the amino alcohol derivative represented by the general formula (1) is 1-benzyl-3-pyrrolidinol.
- 9. The production method according to claim 2,wherein the amino alcohol derivative represented by the general formula (1) is in an optically active form and the sulfonic acid ester derivative represented by the general formula (4) is in an optically active form.
- 10. The production method according to claim 9,wherein the aprotic organic solvent is toluene.
- 11. The production method according to claim 2,wherein the aprotic organic solvent is toluene.
- 12. The production method according to claim 2,wherein the non-water-prohibiting inorganic base comprises at least one species selected from the group consisting of lithium hydroxide, sodium hydroxide, potassium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate.
- 13. The production method according to claim 3,wherein the non-water-prohibiting inorganic base comprises at least one species selected from the group consisting of lithium hydroxide, sodium hydroxide, potassium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate.
- 14. The production method according to claim 4,wherein the non-water-prohibiting inorganic base comprises at least one species selected from the group consisting of lithium hydroxide, sodium hydroxide, potassium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate.
- 15. The production method according to claim 2,wherein the organic sulfonyl halide represented by the general formula (3) is methanesulfonyl chloride.
- 16. The production method according to claim 3,wherein the organic sulfonyl halide represented by the general formula (3) is methanesulfonyl chloride.
- 17. The production method according to claim 4,wherein the organic sulfonyl halide represented by the general formula (3) is methanesulfonyl chloride.
- 18. The production method according to claim 5,wherein the organic sulfonyl halide represented by the general formula (3) is methanesulfonyl chloride.
- 19. The production method according to claim 6,wherein the organic sulfonyl halide represented by the general formula (3) is methanesulfonyl chloride.
- 20. The production method according to claim 2,wherein the amino alcohol derivative represented by the general formula (1) is 1-benzyl-3-pyrrolidinol.
- 21. The production method according to claim 3,wherein the amino alcohol derivative represented by the general formula (1) is 1-benzyl-3-pyrrolidinol.
- 22. The production method according to claim 4,wherein the amino alcohol derivative represented by the general formula (1) is 1-benzyl-3-pyrrolidinol.
- 23. The production method according to claim 5,wherein the amino alcohol derivative represented by the general formula (1) is 1-benzyl-3-pyrrolidinol.
- 24. The production method according to claim 6,wherein the amino alcohol derivative represented by the general formula (1) is 1-benzyl-3-pyrrolidinol.
- 25. The production method according to claim 7,wherein the amino alcohol derivative represented by the general formula (1) is 1-benzyl-3-pyrrolidinol.
CROSS REFERENCE TO RELATED APPLICATIONS
This application is a continuation of PCT/JP00/08277, filed Nov. 24, 2000, and claims priority to JP 2000-172509, filed Jun. 8, 2000.
Foreign Referenced Citations (6)
Number |
Date |
Country |
61-207370 |
Sep 1986 |
JP |
62-240651 |
Oct 1987 |
JP |
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JP |
4-25946 |
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JP |
9-202763 |
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JP |
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WO |
Non-Patent Literature Citations (2)
Entry |
Yamada Koichiro, et al., Production of optically active 1-substituted-2-aminopropane, Oct. 21, 1987, JP 62-240651. |
Kutsuki Hidetoshi, et al., Production of optically active 1-Benzyl-3-hydroxypyrrolidine, Jun. 6, 1989, JP01-143852. |