Novel processes for the preparation of bicyclic aminoalcohols
AssigneeShionogi & Co., Ltd.
InventorsTsunetoshi Honma, Yoshiharu Hiramatsu, 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. 1
Claims13
A process for the preparation of a compound (II):
- 54
- wherein R1 is alkyl, which comprises reacting a compound (I):
- 55
- with XCH2COOR1 wherein X is halogen, and R1 is as defined above in the presence of an additive and a base.
A process for the preparation of a compound (IV):
- 56
- which comprises reducing a compound (III):
- 57
- wherein R1 is as defined above, and R2 is hydrogen or alkyl, with an aluminum hydride,
A process for the preparation of a compound (IV):
- 58
- which comprises reacting a compound (II):
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- wherein R1 is as defined above, with NH2OR2 wherein R2 is as defined above to give a compound (III):
- 60
- wherein R1 and R2 are as defined above, and reducing the compound (III) with an aluminum hydride.
A process for the preparation of a compound (IX):
- 65
- wherein R5 each is independently alkyl, which comprises reacting a compound (I):
- 66
- with (R5)3SiX wherein R5 is as defined above, and X is halogen, in the presence of a base.
A process for the preparation of a compound (X):
- 67
- wherein R6 each is independently alkyl, which comprises reacting a compound (IX):
- 68
- wherein R5 each is independently alkyl, with CH2═CHOR6 wherein R6 is as defined above in the presence of ceric ammonium nitrate (IV) in a solvate of R6OH wherein R6 is as defined above.
Dependencies are inferred from the claim text.