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1. WO1990014342 - SUBSTITUTED ISOXAZOLIDINES AND ISOXAZOLINES

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[ EN ]

CLAIMS

1. a) Process for the preparation of delmopinol comprising reacting a mono- or polyunsaturated 4-propyl- heptyl compound having the formula I or II:

I: CH2=CH-R II: CH=C-R

wherein R is 2-propylpentyl optionally with one,
two or three internal unsaturated bonds, or
2-substituted-2-propylpentyl optionally having one or two internal unsaturated bonds wherein the
2-substituent is a leaving group;

b) reacting the mono- and polyunsaturated 4-propyl- heptyl compound (I and II) with a morpholine nitro¬



III
to produce the compounds IV or V:


wherein R is a previously defined;

c) reductive ringopening of the compounds IV and V to the compounds Via, VIb and Vic having the formulas:

Via


VIb Vic
d) transferring Vib and Vic to the corresponding chlo- roanalogs;
e) transferring the compounds of step d) to the compound Via and
f) alkylating the compound Via to delmopinol
(3-(4-propylpentyl )-morphol ine-ethanol ) .

2. Process according to claim 1 characterized in that the leaving group is selected from hydroxy, alkoxy, acetoxy or tetrahydropyrany oxy.

3. Process according to claim 1 characterized in that the unsaturated compound has formula I and that R is
2-propylpentyl, 2-propyl-l-pentenyl , 2-propyl-2-pentenyl or 2-hydroxy-2-propylpentyl.

4. Process according to claim 1 characterized in that the unsaturated compound has formula II and that R is
2-prop lpentyl.

5. Intermediates having the formulas:




IV-syn wherein R is 2-propylpent 1 optionally with one, two or three internal unsaturated bonds, or 2-substituted- 2-propylpentyl optionally with one or two internal unsaturated bonds wherein the 2-substituent is a leaving group.

6. Intermediates according to claim 5 characterized in that the leaving group is selected from hydroxy, al oxy, acetoxy or tetrahydropyranyloxy.

7. Intermediates according to claim 5 characterized in that it has formula IV wherein R is 2-propylpentyl, 2-propyl- 1-pentenyl, 2-propyl-2-pentenyl or 2-hydroxy-2-propyl- pentyl .

8. Intermediates according to claim 5 characterized in that it has formula V wherein R is 2-propylpent 1.