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US 6,723,857 B1Granted
Processes for the preparation of bicyclic aminoalcohols
AssigneeShionogi & Co., Ltd.
InventorsTsunetoshi Honma, Hiramatsu Yoshiharu, Susumu Mitsumori
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Abstract
The present invention provides a process for the preparation of a bicyclic aminoalcohol which comprises reacting a starting compound, nopinone (I), with XCH2COOR1 wherein X is halogen, and R1 is alkyl, in the presence of an additive and a base to produce a compound (II), converting it to oxime derivative (III), and reducing it with an aluminum hydride.
Claims9
A process for the preparation of a compound (VI):
- wherein R3 is hydrogen, alkyl, acyl, alkylsulfonyl or arylsulfonyl, which comprises reducing a compound (III):
- wherein R1 is alkyl, and R2 is hydrogen or alkyl, with an aluminum hydride to prepare a compound (IV):
- and reacting the compound (IV) or its salt with a compound (V):
- wherein R3 is as defined above or its reactive derivative.
1 more element
A process for the preparation of a compound (VI):
- wherein R3 is hydrogen, alkyl, acyl, alkylsulfonyl or arylsulfonyl, which comprises reacting a compound (II):
- wherein R1 is alkyl, with NH2OR2 wherein R2 is hydrogen or alkyl to give a compound (III):
- wherein R1 and R2 are as defined above, reducing the compound (III) with an aluminum hydride to prepare a compound (IV):
- and reacting the compound (IV) or its salt with a compound (V):
- wherein R3 is as defined above or its reactive derivative.
2 more elements
A process for the preparation of a compound (VI):
- wherein R3 is hydrogen, alkyl, acyl, alkylsulfonyl or arylsulfonyl, which comprises reacting a compound (I):
- with XCH2COOR1 wherein X is halogen, and R1 is alkyl, in the presence of an additive selected from the group consisting of N,N′-dimethylpropyleneurea and 1,3-dimethyl-2-imidazolidinone and a base to prepare a compound (II):
- wherein R1 is as defined above, reacting the compound (II) with NH2OR2 wherein R2 is hydrogen or alkyl to prepare a compound (III):
- wherein R1 and R2 are as defined above, reducing the compound (III) with an aluminum hydride to prepare a compound (IV):
- and reacting the compound (IV) or its salt with a compound (V):
- wherein R3 is as defined above or its reactive derivative.
3 more elements
A process for the preparation of a compound (VII):
- wherein R3 is hydrogen, alkyl, acyl, alkylsulfonyl or arylsulfonyl, which comprises reacting a compound (IX):
- wherein R5 each is independently alkyl, with CH2═CHOR6 wherein R6 is alkyl, in the presence of ceric ammonium nitrate (IV) in a solvent of R6OH wherein R6 is as defined above to prepare a compound (X):
- wherein R6 each is independently alkyl, reacting the compound (X) with NH2OR2 wherein R2 is hydrogen or alkyl, to give a compound (XI):
- wherein R2 and R6 are as defined above, reducing the compound (XI) to give a compound (XII):
- wherein R6 is as defined above, reacting the compound (XII) with a compound (V):
- wherein R3 is as defined above or its reactive derivative to give a compound (XIII):
- wherein R3 and R6 are as defined above, and reacting the compound (XIII) with an acid.
4 more elements
Dependencies are inferred from the claim text.