An efficient synthesis of an NMDA receptor antagonist via stereoselective fluorination

Synthesis

Volumn , Issue 6, 2008, Pages 891-896

  Bio, Matthew M ^a   Waters, Marjorie ^b   Javadi, Gary ^b   Song, Zhiguo Jake ^b   Zhang, Fei ^b   Thomas, Dave ^b  

^a AMGEN INC   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Deoxygenation; Ethers; Fluorine; Heterocycles; Stereoselective synthesis

Indexed keywords

BENZYLIC FLUORIDE; HETEROCYCLES; REAGENTS; STEREOSELECTIVE SYNTHESIS;

ALCOHOLS; EPOXIDATION; ETHERS; FLUORINATION; FLUORINE; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

SULFUR COMPOUNDS;

BENZYL ALCOHOL; EPOXIDE; FLUORIDE; N [4 [2 FLUORO 2 (2 FLUOROPHENYL)ETHOXY]CYCLOHEXYL] 1H PYRAZOLO[3,4 D]PYRIMIDIN 4 AMINE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; PYRAZOLO[3,4 D]PYRIMIDINE DERIVATIVE; REAGENT; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; FLUORINATION; METHODOLOGY; STEREOCHEMISTRY;

EID: 41349089526     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032181     Document Type: Article

References (25)

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24. This salt formation improved the enantiomeric purity of (R)-2 to 98.4% ee, which was critical for preparing the final product with the required high optical purity.
25. The polymerization resulting from reaction of 3 with itself via displacement of the chloride by the pyrrazole ring nitrogen of another molecule of 3 (Scheme 7). (Chemical Equation Presented)