Title:
METHOD FOR SYNTHESIZING (1R)-1-(2,2-DIMETHYL-4H-1,3-BENZODIOXIN-6-YL)-2-NITROETHANOL
Document Type and Number:
WIPO Patent Application WO/2023/097696
Kind Code:
A1
Abstract:
Disclosed is a method for synthesizing (1R)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-nitroethanol. The route of the method is as follows: The method is used for synthesizing (1R)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-nitroethanol, which is used in the preparation of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one, such that reaction steps can be shortened. The method has the advantages of having a high reaction turnover number, high atom economy, being suitable for industrial production, etc. Compared with a currently reported synthetic route using the asymmetric Henry reaction, the price of a catalyst required for the present synthetic route is relatively low, the molar yield in the step of reducing α-nitroketone is greater than 85%, and the present synthetic route has the characteristics of high asymmetric selectivity and being easy to produce.
Inventors:
PHILLIS ANDREW TOROA (CN)
YE WEIPING (CN)
ZHOU ZHANGTAO (CN)
CHEN JIANMING (CN)
WANG DAOGONG (CN)
LUO FUYUAN (CN)
YE WEIPING (CN)
ZHOU ZHANGTAO (CN)
CHEN JIANMING (CN)
WANG DAOGONG (CN)
LUO FUYUAN (CN)
Application Number:
PCT/CN2021/135535
Publication Date:
June 08, 2023
Filing Date:
December 03, 2021
Export Citation:
Assignee:
GUANGDONG RAFFLES PHARMATECH CO LTD (CN)
International Classes:
C07D319/08; B01J31/02; B01J31/06; B01J31/18; B01J31/22; C07B53/00
Foreign References:
| US20030171592A1 | 2003-09-11 |
Other References:
GUO, ZONGLIANG ET AL.: "Enantioselective synthesis of (R)-salmeterol employing an asymmetric Henry reaction as the key step", TETRAHEDRON ASYMMETRY, vol. 22, no. 13, 6 September 2011 (2011-09-06), pages 1395 - 1399, XP028298696, DOI: 10.1016/j.tetasy.2011.08.008
KAKESH, N. ET AL.: "Imidazolium-Based Ionic Network as a Robust Heterogeneous Catalyst in Synthesis of Phenacyl Derivatives", RUSSIAN JOURNAL OF GENERAL CHEMISTRY, vol. 89, no. 6, 31 December 2019 (2019-12-31), pages 1218 - 1220, XP036833619, DOI: 10.1134/S1070363219060185
WATANABE, MASAHITO ET AL.: "Practical Synthesis of Optically Active Amino Alcohols via Asymmetric Transfer Hydrogenation of Functionalized Aromatic Ketones", JOURNAL OF ORGANIC CHEMISTRY, vol. 67, no. 5, 8 February 2002 (2002-02-08), pages 1712 - 1715, XP002229950, DOI: 10.1021/jo011076w
HAMADA, T. TORII, T. IZAWA, K. IKARIYA, T.: "A practical synthesis of optically active aromatic epoxides via asymmetric transfer hydrogenation of @a-chlorinated ketones with chiral rhodium-diamine catalyst", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 60, no. 34, 16 August 2004 (2004-08-16), AMSTERDAM, NL , pages 7411 - 7417, XP004547491, ISSN: 0040-4020, DOI: 10.1016/j.tet.2004.06.076
KAKESH, N. ET AL.: "Imidazolium-Based Ionic Network as a Robust Heterogeneous Catalyst in Synthesis of Phenacyl Derivatives", RUSSIAN JOURNAL OF GENERAL CHEMISTRY, vol. 89, no. 6, 31 December 2019 (2019-12-31), pages 1218 - 1220, XP036833619, DOI: 10.1134/S1070363219060185
WATANABE, MASAHITO ET AL.: "Practical Synthesis of Optically Active Amino Alcohols via Asymmetric Transfer Hydrogenation of Functionalized Aromatic Ketones", JOURNAL OF ORGANIC CHEMISTRY, vol. 67, no. 5, 8 February 2002 (2002-02-08), pages 1712 - 1715, XP002229950, DOI: 10.1021/jo011076w
HAMADA, T. TORII, T. IZAWA, K. IKARIYA, T.: "A practical synthesis of optically active aromatic epoxides via asymmetric transfer hydrogenation of @a-chlorinated ketones with chiral rhodium-diamine catalyst", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 60, no. 34, 16 August 2004 (2004-08-16), AMSTERDAM, NL , pages 7411 - 7417, XP004547491, ISSN: 0040-4020, DOI: 10.1016/j.tet.2004.06.076
Attorney, Agent or Firm:
BEIJING ORIGINTELLIGENCE IP LAW FIRM (CN)
Download PDF: