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US 10,377,732 B2Granted
Process for preparing aminotetrahydropyrans
AssigneeF.I.S. Fabbrica Italiana Sintetici S.p.A.
InventorsPaolo Maragni, Massimo Verzini
Life of this patent
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Abstract
The present invention relates to a process for preparing 3-amino tetrahydropyrans and, more particularly, to an improved method for synthesizing a 2,3,5-substituted tetrahydropyran derivative, intermediate being used in the preparation of dipeptidyl peptidase-IV enzyme inhibitors (DPP-4 inhibitors).
Claims18
A process for preparing a compound of formula (I):
- wherein Ar is phenyl optionally substituted with one to five R substituents,
- each R is independently selected from halogen, (C1-C4)-alkyl, optionally substituted by halogen, or (C1-C4)-alkoxy, optionally substituted by halogen;
- and P is a primary amine protecting group;
- the process comprising:
- a) reacting, in the presence of a basic species or a catalyst, a compound of formula (II):
- wherein each R1 and R2 is independently hydrogen or (C1-C4)-alkyl,
- or, wherein R1 and R2, when taken together, form a (C3-C7)-cycloalkyl group;
- with a compound of formula (III):
- Ar—CHO (III)
- wherein Ar is as defined above;
- to give a compound of formula (IV):
- wherein Ar, R1 and R2 are as defined above;
- and
- b) converting a compound of formula (IV) into a compound of formula (I).
11 more elements
A compound of formula (IV):
- wherein Ar is phenyl, optionally substituted with one to five substituents,
- each R is independently selected from halogen, (C1-C4)-alkyl, optionally substituted by halogen, or (C1-C4)-alkoxy, optionally substituted by halogen;
- and
- wherein each R1 and R2 is independently hydrogen or (C1-C4)-alkyl,
- or wherein R1 and R2, when taken together, form a (C3-C7)-cycloalkyl group.
2 more elements
A compound having a formula:
- 1-(2,5-difluorophenyl)-2-nitro-3((S)-1,4-dioxaspiro[4.5]decan-2-yl)propan-1-ol (IV)
- or
- 1-(2,4,5-trifluorophenyl)-2-nitro-3-((S)-1,4-dioxaspiro[4.5]decan-2-yl)propan-1-ol (IV).
A process for preparing a compound of formula (IV):
- wherein Ar is phenyl optionally substituted with one to five R substituents, each R is independently selected from halogen, (C1-C4)-alkyl, optionally substituted by halogen, or (C1-C4)-alkoxy, optionally substituted by halogen;
- wherein each R1 and R2 is independently hydrogen or (C1-C4)-alkyl, or, wherein R1 and R2, when taken together, form a (C3-C7)-cycloalkyl group;
- the process comprising:
- a) reacting, in the presence of a basic species or a catalyst, a compound of formula (II):
- wherein R1 and R2 are as defined above;
- with a compound of formula (III):
- Ar—CHO (III)
- wherein Ar is as defined above.
5 more elements
Dependencies are inferred from the claim text.