4-propylcyclohexan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (R)-4-(6-Hydroxynaphthalen-2-yl)-4-methyl-oxazolidin-2-one (Example 4, 0.301 g, 0.00124 mol) was dissolved in tetrahydrofuran (5.00 mL, 0.0616 mol). 4-Propylcyclohexanol (0.211 g, 0.00148 mol) and triphenylphosphine polymer-bound (1.07 g, 0.00198 mol) were added and the mixture was stirred at room temperature. Diisopropyl azodicarboxylate (0.390 mL, 0.00198 mol) was then added and the mixture was stirred for 2 days at room temperature. The mixture was filtered through CELITE™, concentrated and purified by flash chromatography (0-30% EtOAc in methylene chloride) to give 0.4942 g of the title product (109% yield). the mixture was stirred for 2 days at room temperature The mixture was filtered through CELITE™ concentrated purified by flash chromatography (0-30% EtOAc in methylene chloride)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.49 g of 1-(4-carboxycyclohexyl)-4-pentylpiperidine (m.p. 208°) is boiled for 1 hour together with 2.4 g of SOCl2 ; the mixture is evaporated to dryness; the crude acid chloride obtained is dissolved in 15 ml of toluene; 1 ml of pyridine and 1.42 g of 4-propylcyclohexanol are added; and the mixture is boiled for 2 hours. Water is then added. The phases are separated, and the organic phase is washed with water, dried over Na2SO4 and evaporated to dryness, to give 1-[trans-4-(trans-4-propylcyclohexyloxycarbonyl)-cyclohexyl]-4-pentylpiperidine. the mixture is evaporated to dryness the crude acid chloride obtained The phases are separated the organic phase is washed with water dried over Na2SO4 evaporated to dryness

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (R)-4-(6-Hydroxynaphthalen-2-yl)-4-methyl-oxazolidin-2-one (Example 4, 0.301 g, 0.00124 mol) was dissolved in tetrahydrofuran (5.00 mL, 0.0616 mol). 4-Propylcyclohexanol (0.211 g, 0.00148 mol) and triphenylphosphine polymer-bound (1.07 g, 0.00198 mol) were added and the mixture was stirred at room temperature. Diisopropyl azodicarboxylate (0.390 mL, 0.00198 mol) was then added and the mixture was stirred for 2 days at room temperature. The mixture was filtered through CELITE™, concentrated and purified by flash chromatography (0-30% EtOAc in methylene chloride) to give 0.4942 g of to the title product (109% yield). the mixture was stirred for 2 days at room temperature The mixture was filtered through CELITE™ concentrated purified by flash chromatography (0-30% EtOAc in methylene chloride)