A new synthesis of spiropyrrolidine-tetralones via an unexpected formal ring-contraction of 4-disubstituted piperidine to 3-disubstituted pyrrolidine

Tetrahedron Letters

Volumn 51, Issue 49, 2010, Pages 6415-6417

  Bandarage, Upul K ^a   Davies, Robert J ^a  

^a VERTEX PHARMACEUTICALS   (United States)

Author keywords

Indanone; Intramolecular quaternization; Spiropiperidine; Spiropyrrolidine; Tetralone

Indexed keywords

1 TETRALONE DERIVATIVE; PIPERIDINE; PYRROLIDINE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; RACEMIC MIXTURE; SYNTHESIS;

EID: 78149285940     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.142     Document Type: Article

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10. 3OD, 500 MHz) δ 8.05-8.08 (m, 1H), 7.07-7.14 (m, 2H), 3.68 (m, 1H), 3.58 (m, 1H), 3.50-3.53 (m, 2H), 2.68-2.78 (m, 2H), 2.21-2.25 (m, 3H), 2.08-2.19 (m, 1H), 150 (s, 9H).
11. 3OD, 500 MHz) δ 7.73 (dd, J = 8.5, 5.3 Hz, 1H), 7.39 (dd, J = 9.1, 2.2 Hz, 1H), 7.19 (t m, 1H), 4.18 (m, 2H), 2.94 (s, 2H), 2.74 (s, 2H), 1.97 (m, 2H), 1.55 (m, 2H), 1.49 (s, 9H).