Improved Process for Preparation of (3R,4R)-3-(3,4-Dimethyl-4-piperidinyl)phenol, A Key Intermediate for the Synthesis of Alvimopan

被引：4
|
作者：
Reddy, Beeravalli Ramalinga [1 ]
Reddy, Kikkuru Srirami [1 ]
Dubey, Manoj Kumar [1 ]
Kumari, Y. Bharati [2 ]
Bandichhor, Rakeshwar [1 ]
机构：
[1] Dr Reddys Labs Ltd, Res & Dev, Integrated Prod Dev, Hyderabad 500072, Andhra Pradesh, India
[2] Jawaharlal Nehru Technol Univ, Inst Sci & Technol, Ctr Environm, Hyderabad 500072, Andhra Pradesh, India
来源：
ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2014年 / 18卷 / 01期
关键词：
D O I：
10.1021/op400144z
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
This report discloses an industrially feasible and cost efficient process for the preparation of the compound [(3R, 4R)-3-(3,4-dimethyl-4-piperidinyl)phenol] (1), which is used as the key intermediate for preparation of the opioid drug Alvimopan. The overall yield in this process is increased from IS to 30%, mainly due to the improvement in yield from 26 to 53% for intermediate 7.
引用
收藏
页码：163 / 167
页数：5
相关论文
共 50 条
  • [1] Diastereoselective Preparation of Substituted δ-Valerolactones. Synthesis of (3R,4S)- and (3R,4R)-Simplactones
    Osorio-Lozada, Antonio
    Olivo, Horacio F.
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03): : 1360 - 1363
  • [2] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (-)-TRANS(3R,4R)-3,4-DIMETHYLCYCLOHEXANONE
    MILHAVET, JC
    SABLAYROLLES, C
    CHAPAT, JP
    GRANGER, R
    JOURNAL OF CHEMICAL RESEARCH-S, 1978, (08): : 291 - &
  • [3] (3R,4R)-4-叠氮基-3-哌啶醇的合成
    刘生丽
    王晓霞
    李卫平
    陈文秀
    李松芳
    刘荣
    兰州理工大学学报, 2019, 45 (03) : 73 - 76
  • [4] A concise, stereoselective and scalable synthesis of optically pure (3R,4R)-1-benzyl- and (3R,4R)-1-Boc-3-methyl-4-aminopiperidines
    Hazra, Sunit
    Kangune, Ankit
    Pawar, Govind
    Karmakar, Ananta
    Pabbisetty, Kumar B.
    Mortensen, Deborah S.
    Dodd, Dharmpal S.
    Li, Jianqing
    Mathur, Arvind
    Gupta, Anuradha
    Nimje, Roshan Y.
    TETRAHEDRON, 2024, 167
  • [5] Pentafluorophenyl (3R,4R,5R)-5-{[(3R,4R,5R)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydro-furan-3-carbonylamino]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate
    Punzo, F
    Cowley, AR
    Watkin, DJ
    Simone, MI
    Edwards, AA
    Tranter, GE
    Fleet, GWJ
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2006, 62 : O473 - O475
  • [6] Novel synthesis of (3R,4R)-4-acetoxy-3-[1′(R)-tert-butyldimethylsilyloxyethyl]azetidin-2-one:: A key intermediate for penem and carbapenem synthesis
    Singh, Santosh Kumar
    Singh, G. B.
    Byri, V. K.
    Satish, B.
    Dhamjewar, Ravi
    Gopalan, B.
    SYNTHETIC COMMUNICATIONS, 2008, 38 (03) : 456 - 464
  • [7] Asymmetric synthesis of the novel H3 agonist (+)-(3R,4R)-3-(4-imidazolyl)-4-methylpyrrolidine, dihydrochloride.
    Aslanian, R
    Lee, G
    Iyer, RV
    Shih, NY
    Piwinski, JJ
    Draper, RW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U51 - U51
  • [8] PRACTICAL SYNTHESIS OF (3R,4R)-4-ACETOXY-3-[1(R)-TERT-BUTYLDIMETHYLSILYLOXYETHYL]AZETIDIN-2-ONE - A KEY INTERMEDIATE FOR PENEM AND CARBAPENEM SYNTHESIS
    ENDO, M
    SYNTHETIC COMMUNICATIONS, 1987, 17 (09) : 1029 - 1033
  • [9] A short, stereoselective synthesis of (3R,4R)-4-acetoxy-3-[(R)-1′((t-butyldimethylsilyl)oxy)ethyl]-2-azetidinone, key intermediate for the preparation of carbapenem antibiotics
    Cozzi, F
    Annunziata, R
    Cinquini, M
    Poletti, L
    Perboni, A
    Tamburini, B
    CHIRALITY, 1998, 10 (1-2) : 91 - 94
  • [10] SYNTHESIS OF (3R,4R)-3-AMINO-4-HYDROXYHEXAHYDROAZEPINE, THE CHIRAL CONSTITUENT OF THE ANTIBIOTIC OPHIOCORDIN
    MULLER, A
    TAKYAR, DK
    WITT, S
    KONIG, WA
    LIEBIGS ANNALEN DER CHEMIE, 1993, (06): : 651 - 655
12345