Process for preparing substituted 8-azabicyclo[3.2.1]octan-3-ols
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United States of America Patent
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Dec 2, 2008
Grant Date -
Mar 16, 2006
app pub date -
Sep 13, 2005
filing date -
Sep 15, 2004
priority date (Note) -
Expired
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Abstract
The present invention relates to a process for preparing substituted 8-azabicyclo[3.2.1]octan-3-ols having the structural formula I ##STR00001## or a pharmaceutically acceptable salt or solvate thereof, wherein R is benzyl, R.sup.5-benzyl, allyl, --C(O)R.sup.6, --C(O)OR.sup.8 or --CH(R.sup.7).sub.2; R.sup.1 is optionally substituted aryl or optionally substituted heteroaryl; and R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are as defined in the specification; comprising a) reacting an amine of formula II R--NH.sub.2 II with 2,5-dimethoxytetrahydrofuran or HC(O)(CH.sub.2).sub.2C(O)H, and C(O)(CH.sub.2C(O)OR.sup.4).sub.2, wherein R.sup.4 is H or alkyl, to obtain a compound of formula III ##STR00002## b) reacting a compound of formula III with I-R.sup.1, alkyl lithium, and optionally a lithium salt, to obtain a compound of formula I; and c) optionally converting a compound of formula I wherein R is benzyl, R.sup.5-benzyl, allyl, --C(O)R.sup.6 or --C(O)OR.sup.8 to a compound of formula I wherein R is --CH(R.sup.7).sub.2. Intermediates in the process are also claimed.
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