An asymmetric synthesis of (2S,5S)-5-substituted azepane-2-carboxylate derivatives

Journal of Organic Chemistry

Volumn 76, Issue 6, 2011, Pages 1937-1940

  Wishka, Donn G ^a   Bédard, Marion ^d   Brighty, Katherine E ^d   Buzon, Richard A ^d   Farley, Kathleen A ^d   Fichtner, Michael W ^d   Kauffman, Goss S ^d   Kooistra, Jaap ^b   Lewis, Jason G ^c   O'Dowd, Hardwin ^c   Samardjiev, Ivan J ^d   Samas, Brian ^d   Yalamanchi, Geeta ^d   Noe, Mark C ^d  

^a PFIZER INC   (United States)

^b Syncom BV   (Netherlands)

^c Vicuron Pharmaceuticals   (United States)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; DRUG DISCOVERY; LARGE SCALE PREPARATION; OXIDATIVE CLEAVAGES; STEREOSELECTIVE MANNER;

KETONES;

CARBOXYLATION;

(2,5) 5 SUBSTITUTED AZEPANE 2 CARBOXYLATE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

BICYCLO COMPOUNDS, HETEROCYCLIC; CARBOXYLIC ACIDS; DRUG DISCOVERY; KETONES;

EID: 79953885690     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102475s     Document Type: Article

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25. For a single crystal (0.32 × 0.18 × 0.14 mm3) of (1S,5S)-3Hspiro[ 4-azabicyclo[3.2.2]nonane-6,2′-[1,3]dioxolane]-3-thione, X-ray intensity data were collected at 299 K on a Bruker-AXS APEX2 diffractometer. A total of 1919 independent reflections were observed. Laue symmetry revealed an orthorhombic crystal system with the following unit cell dimensions: a = 6.9899(2) Å, b = 22.4792(7) Å, c =6.8185(3) Å; volume = 1071.37(7) Å3; Z = 4; Dcalc = 1.322 Mg/m3. The space group was assigned as P21212. The structure was solved by direct methods, using the SHELXTL suite. All non-hydrogen atoms were refined with anisotropic thermal parameters. The hydrogen atom located on N2 was found from the Fourier difference map and refined freely. All remaining hydrogen atoms were fixed in idealized positions. The final model refined to a goodness fit of 1.148 with R1 = 0.0778 (I > 2 σ) and wR2 = 0.1614. Absolute configuration was assigned based on a Flack parameter of 0.01(3).
26. We gratefully acknowledge Professor E .J. Corey for the extremely useful and timely suggestion of these reaction conditions.
27. Failure to deactivate the silica gel (0.5-1.0% Et3N) used in the final purification of 14 results in significant disproportionation on the column to give mixtures of compound 14, dimethyl ketal, and ketone.