Title:
METHOD FOR PREPARING HYDROXYL COMPOUND, DEUTERATED COMPOUND THEREOF, AND TRITIATED COMPOUND THEREOF
Document Type and Number:
WIPO Patent Application WO/2021/093556
Kind Code:
A1
Abstract:
Disclosed is a method for preparing a compound I. The method comprises a reaction system comprising a compound II, which contains a carbon-oxygen double bond, and further comprising water, deuterated water, or tritiated water, which is prepared in order to obtain compound I. The method comprises reacting compound II containing the carbon-oxygen double bond with water, deuterated water, or tritiated water in the presence of metallic magnesium and an alkyl halide. The method is the first to use metallic magnesium as a reducing agent and an alkyl halide as an initiator to achieve polarity reversal of a carbonyl compound; the carbonyl compound is further reduced to prepare a compound I core skeleton comprising a hydroxyl-containing compound, a deuterated compound or a tritiated compound thereof.
Inventors:
BAO HONGLI (CN)
ZHU NENGBO (CN)
ZHU NENGBO (CN)
Application Number:
PCT/CN2020/123287
Publication Date:
May 20, 2021
Filing Date:
October 23, 2020
Export Citation:
Assignee:
FUJIAN INST RES STR MATTER CAS (CN)
International Classes:
C07B59/00; C07C29/143; C07C43/23; C07D213/38
Domestic Patent References:
| WO2005115996A1 | 2005-12-08 |
Foreign References:
| CN110015985A | 2019-07-16 | |||
| CN110128233A | 2019-08-16 |
Other References:
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YAMASAKI RYU, IKEDA HIROKAZU, MASU HYUMA, AZUMAYA ISAO, SAITO SHINICHI: "Synthesis and properties of phenylogous amides", TETRAHEDRON, vol. 68, no. 40, 7 October 2012 (2012-10-07), pages 8450 - 8456, XP055812879, ISSN: 0040-4020, DOI: 10.1016/j.tet.2012.07.084
EDUARDO BUSTO , VICENTE GOTOR-FERNANDEZ , VICENTE GOTOR: "Biocatalytic preparation of optically active 4-(N, N-dimethylamino)pyridines for application in chemical asymmetric catalysis", TETRAHEDRON ASYMMETRY, vol. 17, no. 6, 20 March 2006 (2006-03-20), pages 1007 - 1016, XP024962163, ISSN: 0957-4166, DOI: 10.1016/j.tetasy.2006.03.018
ZHU NENGBO, SU MIN, WAN WEN-MING, LI YAJUN, BAO HONGLI: "Practical Method for Reductive Deuteration of Ketones with Magnesium and D2O", ORGANIC LETTERS, vol. 22, no. 3, 22 January 2020 (2020-01-22), pages 991 - 996, XP055812878, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.9b04536
IMAMOTO T , TAKIYAMA N , NAKAMURA K: "Cerium chloride-promoted nucleophilic addition of grignard reagents to ketones an efficient method for the synthesis of tertiary alcohols", TETRAHEDRON LETTERS, vol. 26, no. 39, 31 December 1985 (1985-12-31), pages 4763 - 4766, XP002947214, DOI: 10.1016/S0040-4039(00)94945-1
YAMASAKI RYU, IKEDA HIROKAZU, MASU HYUMA, AZUMAYA ISAO, SAITO SHINICHI: "Synthesis and properties of phenylogous amides", TETRAHEDRON, vol. 68, no. 40, 7 October 2012 (2012-10-07), pages 8450 - 8456, XP055812879, ISSN: 0040-4020, DOI: 10.1016/j.tet.2012.07.084
EDUARDO BUSTO , VICENTE GOTOR-FERNANDEZ , VICENTE GOTOR: "Biocatalytic preparation of optically active 4-(N, N-dimethylamino)pyridines for application in chemical asymmetric catalysis", TETRAHEDRON ASYMMETRY, vol. 17, no. 6, 20 March 2006 (2006-03-20), pages 1007 - 1016, XP024962163, ISSN: 0957-4166, DOI: 10.1016/j.tetasy.2006.03.018
ZHU NENGBO, SU MIN, WAN WEN-MING, LI YAJUN, BAO HONGLI: "Practical Method for Reductive Deuteration of Ketones with Magnesium and D2O", ORGANIC LETTERS, vol. 22, no. 3, 22 January 2020 (2020-01-22), pages 991 - 996, XP055812878, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.9b04536
IMAMOTO T , TAKIYAMA N , NAKAMURA K: "Cerium chloride-promoted nucleophilic addition of grignard reagents to ketones an efficient method for the synthesis of tertiary alcohols", TETRAHEDRON LETTERS, vol. 26, no. 39, 31 December 1985 (1985-12-31), pages 4763 - 4766, XP002947214, DOI: 10.1016/S0040-4039(00)94945-1
Attorney, Agent or Firm:
PERIODIC LAW FIRM (CN)
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