Process for preparing delmopinol via the intermediates isoxazolidines and isoxazolines

A process for preparing 3-(4-propylpentyl)-morpholine-ethanol (delmopinol) comprising:

• a) reacting a mono- or polyunsaturated 4-propylheptyl compound having the formula I or II:
• I. CH.sub.2 .dbd.CH--R II. CH.tbd.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 with a morpholine nitrone (III) ##STR15## to produce the compounds of the formula:
• ##STR16## b) reductive ring opening of compounds IV or V to compounds of the formulas:
• ##STR17## c) reacting the mixture of VIb and VIc with a chlorinating agent;
• d) dechlorinating the compounds of step c) to the compound VIa by hydrogenating;
• and
• e) alkylating the compound VIa to render delmopinol.