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US 2014/0228578 A1Published application
Chiral Synthesis of Pyrrolidine Core Compounds en route to Neuronal Nitric Oxide Synthase Inhibitors
AssigneeNorthwestern University
InventorsRichard B. Silverman, Fengtian Xue
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Abstract
A chiral synthesis of pyrrolidine compounds en route to selective neuronal nitric oxide synthase inhibitors, and representative inhibitor compounds heretofore unattainable.
Claims17
A method of preparing a chiral pyrrolidine core compound, said method comprising:
- providing an N-Boc-protected pyrrolidine-3,4-epoxide;
- alkylating said epoxide with an N-Boc-protected, amino-substituted haloalkylheterocyclic compound, said alkylation providing a racemic alkyl-substituted trans-pyrrolidine alcohol;
- protecting said amino group on said heterocyclic substituent with a Boc reagent;
- resolving said racemic trans-alcohol by camphanic acid esterification, to provide separable diastereomers;
- and
- hydrolysis of one said enantiomer of said racemate, to provide a chiral 4-hydroxypyrrolidine compound.
3 more elements
A method of preparing a chiral pyrrolidine core compound, said method comprising:
- providing a racemic di-N-Boc-protected 3,4-trans-(aminopyridinyl)alkyl-substituted pyrrolidine alcohol;
- protecting said amino group with a Boc reagent, to provide a tri-Boc-protected pyrrolidine compound;
- and
- resolving said racemate by camphanic acid esterification, to provide separable diastereomers.
1 more element
A method of using sequential amino-protection to prepare a chiral pyrrolidine core compound, said method comprising:
- providing a di-N-Boc-protected 3,4-trans-(aminoheterocyclyl)alkyl-substituted pyrrolidine alcohol, said heterocyclyl amino group mono-protected with a Boc moiety;
- protecting said pyrrolidine hydroxy group;
- protecting said aminoheterocyclyl moiety with a Boc reagent;
- deprotecting said hydroxy group;
- and
- racemic resolution by camphanic acid esterification.
3 more elements
Dependencies are inferred from the claim text.