Scalable synthesis and isolation of the four stereoisomers of methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate, useful intermediates for the synthesis of S1P1 receptor agonists

Journal of Organic Chemistry

Volumn 74, Issue 13, 2009, Pages 4886-4889

  Wallace, Grier A ^a   Gordon, Thomas D ^a   Hayes, Martin E ^a   Konopacki, Donald B ^a   Fix Stenzel, Shannon R ^a   Zhang, Xiaolei ^b   Grongsaard, Pintipa ^a   Cusack, Kevin P ^a   Schaffter, Lisa M ^a   Henry, Rodger F ^a   Stoffel, Robert H ^a  

^a ABBOTT LABORATORIES   (United States)

^b GENZYME CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; GRAM QUANTITIES; SCALABLE SYNTHESIS;

AMINATION; ISOMERS; METHANOL; STEREOCHEMISTRY;

AMINES;

[1 AMINO 3 (4 OCTYLPHENYL)CYCLOPENTYL]METHANOL; CARBOXYLIC ACID DERIVATIVE; CYCLOPENTANE DERIVATIVE; METHANOL DERIVATIVE; METHYL 1 AMINO 3 (4 BROMOPHENYL)CYCLOPENTANECARBOXYLATE; SPHINGOSINE 1 PHOSPHATE RECEPTOR; UNCLASSIFIED DRUG;

AGONIST; ARTICLE; CHIRALITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMER; QUANTUM YIELD; STEREOISOMERISM;

CARBOXYLIC ACIDS; CYCLOPENTANES; MOLECULAR STRUCTURE; RECEPTORS, LYSOSPHINGOLIPID; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 67649586373     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900376b     Document Type: Article

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28. Similar results were obtained for both the cis- and trans-diastereomers. For clarity only the cis-isomer is shown in Scheme 4.
29. 13C, mp, and HRMS matched that obtained for ((1R,3R)-5). See the Supporting Information for details of chiral purity analysis.
30. 13C, mp, and HRMS matched that obtained for ((1R,3S)-5). See the Supporting Information for details of chiral purity analysis.