One-Pot Synthesis of Spiro Isochromane-3,3′-piperidines, -3,4′-piperidines and -3,3′-pyrrolidines

J. W. Butcher; D. A. Claremon

doi:10.1055/s-1993-25832

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Synthesis 1993; 1993(2): 211-212
DOI: 10.1055/s-1993-25832

short paper

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One-Pot Synthesis of Spiro Isochromane-3,3′-piperidines, -3,4′-piperidines and -3,3′-pyrrolidines

J. W. Butcher^* , D. A. Claremon

^*Merck Research Laboratories, W26-410, West Point, Pennsylvania 19 486, USA

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Publication Date:
17 September 2002 (online)

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Spiro isochromane-1-ones 1 were treated with lithium aluminum hydride or Grignard reagents to afford diol intermediates 2, which cyclize in 85 % phosphoric acid at 100°C to spiro isochromanes 3 in 72-94 % isolated yields.