(S)-(+)-1-Cyclohexylethylamine → (1R,2R,4S)-2-((1S)-1-cyclohexylethylamino)-1-methyl-4-(1-methylethenyl) cyclohexanol

A 100-mL, single-neck flask equipped with a magnetic stirring bar and a reflux condenser fitted with a nitrogen bubbler was charged with 4.75 g (0.037 mol) of (S)-(−)-1-cyclohexylethylamine, 23.00 g (0.151 mol) of (S)-(−)-limonene oxide, and 2.0 mL of deionized water. The mixture was heated to reflux and held there for 109.75 h. The reaction mixture was cooled to room temperature and filtered to remove an insoluble white solid. The excess limonene oxide was then distilled off at reduced pressure leaving an orange oil that crystallized upon standing over night. The solid was recrystallized from approximately 20 mL of n-heptane to give 3.48 g of (1R,2R,4S)-2-((1S)-1-cyclohexylethylamino)-1-methyl-4-(1-methylethenyl) cyclohexanol, as a white solid, mp 63-64° C.

1. customA 100-mL, single-neck flask equipped with a magnetic stirring bar and a reflux condenser
2. customfitted with a nitrogen bubbler
3. temperatureThe mixture was heated
4. temperatureto reflux
5. filtrationfiltered
6. customto remove an insoluble white solid
7. distillationThe excess limonene oxide was then distilled off at reduced pressure
8. customleaving an orange oil
9. customthat crystallized
10. waitupon standing over night
11. customThe solid was recrystallized from approximately 20 mL of n-heptane

ORD record

ord-b049f668b0604dbbb66e75ffb9d9ced2

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06362373B1