Claims
- 1. A method for the preparation of a compound of formula ##STR13## wherein R represents a hydrogen atom, comprising hydrogenating a compound of formula ##STR14## wherein R represents respectively a group of formula ##STR15## wherein R.sub.1 represents an alkyl group containing 1-4 carbon atoms and Ar represents a phenyl or .alpha.- or .beta.-naphthyl group, optionally substituted by one or more atoms or groups, which may be identical or different, selected from halogen atoms and alkyl groups containing 1-4 carbon atoms, alkoxy groups containing 1 to 4 carbon atoms, or nitro groups, with hydrogen in the presence of a catalyst in an organic solvent selected from aliphatic alcohols containing 1-3 carbon atoms.
- 2. The method according to claim 1 wherein R.sub.1 represents a methyl or ethyl group and Ar represents a phenyl group, optionally substituted by one or more methyl or methoxy groups.
- 3. The method according to claim 1 wherein R.sub.1 represents a methyl group and Ar represents a phenyl group.
- 4. A method for the preparation of a compound of formula VIII ##STR16## wherein R'.sub.1 and R".sub.1, which are identical or different, represent an aliphatic organic acid group containing 2-4 carbon atoms or aromatic acid group, or R'.sub.1 and R".sub.1 taken together form a methylene group whose carbon atom is optionally substituted by one or more groups, which may be identical or different, selected from alkyl groups containing 1-4 carbon atoms, which can be taken together with the carbon atom to which the alkyl groups are attached to form an alicyclic group containing 5 or 6 carbon atoms, or phenyl groups, and G.sub.2 represents a hydrogen atom or a protecting group of an amino group, comprising:
- a) esterifying or acetalating a compound of formula I to protect the hydroxyl moieties thereof: ##STR17## wherein R represents a hydrogen atom or a group of formula II: ##STR18## wherein R.sub.1 represents an alkyl group containing 1-4 carbon atoms and Ar represents a phenyl or .alpha.- or .beta.-naphthyl group, optionally substituted by one or more atoms or groups, which may be identical or different, selected from halogen atoms and alkyl groups containing 1-4 carbon atoms, alkoxy groups containing 1 to 4 carbon atoms, or nitro groups, with hydrogen in the presence of a catalyst in an organic solvent selected from aliphatic alcohols containing 1-3 carbon atoms, to yield a compound of formula VI ##STR19## wherein R, R'.sub.1 and R".sub.1 are defined as above; b) transforming the compound of formula VI to a compound of formula VII: ##STR20## wherein R'.sub.1 and R".sub.1 are defined as above, and G.sub.2 represents a protecting group of the nitrogen atom, by either
- i) hydrogenating the compound of formula VI, in which R represents a group of formula II and protecting the nitrogen atom with a protecting group, wherein the hydrogenating and protecting are optionally conducted simultaneously, or
- ii) protecting the nitrogen atom on the compound of formula VI, wherein R represents a hydrogen atom, with a protecting group; and then
- c) oxidizing the compound of formula VII to the compound of formula VIII.
- 5. The method according to claim 4, wherein the esterifying or acetalating according to step a) is carried out using an aliphatic acid containing 2-4 carbon atoms or an aldehyde or ketone, optionally in the form of an acetal in the presence of an acid in an inert organic solvent at a temperature between 50.degree. C. and the boiling point of the reaction mixture.
- 6. The method according to claim 4, wherein the hydrogenating according to step b) is carried out using hydrogen in the presence of a catalyst.
- 7. The method according to claim 4, wherein when G.sub.2 represents a t-butoxycarbonyl group, the hydrogenating and protecting according to step b) are carried out simultaneously using hydrogen in the presence of a catalyst and di-t-butyl dicarbonate in an aliphatic alcohol containing 1-3 carbon atoms at a temperature between 0.degree. C. and 50.degree. C.
- 8. The method according to claim 4, wherein the oxidizing according to step c) is carried out using RuO.sub.4, which is optionally generated in situ in the presence of an oxidant.
- 9. A method for the preparation of a compound of formula VIII ##STR21## wherein R'.sub.1 and R".sub.1, which are identical or different, represent an aliphatic organic acid group containing 2-4 carbon atoms or aromatic acid group, or R'.sub.1 and R".sub.1 taken together form a methylene group whose carbon atom is optionally substituted by one or more groups, which may be identical or different, selected from alkyl groups containing 1-4 carbon atoms, which can be taken together with the carbon atom to which the alkyl groups are attached to form an alicyclic group containing 5 or 6 carbon atoms, or phenyl groups, and G.sub.2 represents a hydrogen atom or a protecting group of an amino group, comprising oxidizing a compound of formula VI ##STR22## wherein R'.sub.1 and R".sub.1 are defined above and R represents a hydrogen atom, with RuO.sub.4, which is optionally generated in situ in the presence of an oxidant, to obtain a lactam compound, and then protecting the nitrogen of the lactam by reacting the lactam with di-t-butyl dicarbonate in an aliphatic alcohol containing 1-3 carbon atoms at between 0.degree. C. and 50.degree. C.
Priority Claims (1)
Number |
Date |
Country |
Kind |
95 06353 |
May 1995 |
FRX |
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Parent Case Info
This application is a continuation-in-part of U.S. patent application Ser. No. 08/476,156, filed Jun. 7, 1995, now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5364862 |
Spada et al. |
Nov 1994 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
476156 |
Jun 1995 |
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