2,2-dicyclopropylethanol

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

Procedure: This ester is synthesized according to the process described in stage A of Example 4, but replacing the 8-phthalimido-3,6-dioxaoctanoic acid with 6-phthalimidohexanoic acid and the 2,2-dicyclopropylethanol with ethanol.

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the compound of Preparation 155 (1 g, 9.24 mmol) in tetrahydrofuran (15 ml) under nitrogen was added 9-borabicyclo[3.3.1]nonane (18.5 ml of a 0.5M solution in tetrahydrofuran, 1 mol. equiv.) and the solution stirred for 18 hours. Sodium hydroxide (3.08 ml of a 3M aqueous solution, 1 mol. equiv.) was added followed by ethanol (5 ml). The reaction was cooled to 5° C. and hydrogen peroxide (3.14 ml of a 30% w/w aqueous solution, 3 mol. equiv.) added. The reaction was stirred at room temperature for 1 hour. equiv.) was added equiv.) added The reaction was stirred at room temperature for 1 hour

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

Procedure: This ester is synthesized according to the process described in stage A of Example 4, but replacing the 8-phthalimido-3,6-dioxaoctanoic acid with 6-phthalimidohexanoic acid and the 2,2-dicyclopropylethanol with ethanol.

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

Procedure: Dicyclopropyl ethylene (19 g, 0.176 mole) was dissolved in dry tetrahydrofuran (100 ml) in a three-neck flask under nitrogen and treated with borane-tetrahydrofuran in tetrahydrofuran (1M, 210 ml). The mixture was stirred at room temperature for 4 hours before adding cautiously (foaming occurs) 3N sodium hydroxide (60 ml). After addition was complete, aqueous hydrogen peroxide (30%, 60 ml) was added dropwise at a rate sufficient to maintain reflux. When addition was complete, the mixture was refluxed for a further 30 minutes, cooled and the aqueous layer saturated with sodium chloride. The layers were separated, the organic layer dried (MgSO4) and evaporated under reduced pressure to give a quantitative yield of 2,2-dicyclopropylethanol which was pure by GC. (The product could also be distilled, b.p. 99° C./25 mm.) After addition to maintain reflux When addition the mixture was refluxed for a further 30 minutes cooled The layers were separated the organic layer dried (MgSO4) evaporated under reduced pressure

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

Procedure: This ester is synthesized according to the process described in stage A of Example 4, but replacing the 8-phthalimido-3,6-dioxaoctanoic acid with 6-phthalimidohexanoic acid and the 2,2-dicyclopropylethanol with ethanol.

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

Procedure: This ester is synthesized according to the process described in stage A of Example 4, but replacing the 8-phthalimido-3,6-dioxaoctanoic acid with 6-phthalimidohexanoic acid and the 2,2-dicyclopropylethanol with ethanol.