Process for production of quinuclidine compounds
AssigneeDaiichi Sankyo Company, Limited
InventorsYutaka KITAGAWA, Masao FUJITA, Kumiko OTAYA
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Abstract
Provided is a production method for a cis-QMF, which has a low environmental burden and is industrially advantageous. Specifically provided is a production method for a cis-type 2-alkylspiro(1,3-oxathiolane-5,3′)quinuclidine hydrochloride, including: reacting a cis-trans isomer mixture of 2-alkylspiro(1,3-oxathiolane-5,3′)quinuclidine with p-nitrobenzoic acid; resolving the resultant product to produce a cis-type 2-alkylspiro(1,3-oxathiolane-5,3′)quinuclidine p-nitrobenzoate; and converting the p-nitrobenzoate into a hydrochloride.
Claims17
A production method for a cis-type 2-alkylspiro(1,3-oxathiolane-5,3′)quinuclidine hydrochloride, comprising:
- reacting a cis-trans isomer mixture of 2-alkylspiro(1,3-oxathiolane-5,3′)quinuclidine with p-nitrobenzoic acid;
- resolving the resultant product to produce a cis-type 2-alkylspiro(1,3-oxathiolane-5,3′)quinuclidine p-nitrobenzoate;
- and
- converting the p-nitrobenzoate into a hydrochloride.
A production method for a cis-trans isomer mixture of 2-alkylspiro(1,3-oxathiolane-5,3′)quinuclidine, comprising:
- reacting 3-hydroxy-3-mercaptomethylquinuclidine with an aldehyde in an aqueous solvent in the presence of an acid catalyst.
A production method for a cis-trans mixture of 2-alkylspiro(1,3-oxathiolane-5,3′)quinuclidine, comprising:
- reacting a trans-type 2-alkylspiro(1,3-oxathiolane-5,3′)quinuclidine with (a) a boron trifluoride-ether complex and p-nitrobenzoic acid or (b) hydrochloric acid or hydrobromic acid and an aldehyde, in an organic solvent.
A cis-type 2-alkylspiro(1,3-oxathiolane-5,3′)quinuclidine p-nitrobenzoate.
A cis-type 2-methylspiro(1,3-oxathiolane-5,3′)quinuclidine p-nitrobenzoate.
Dependencies are inferred from the claim text.