Sodium Thiosulfate → HCID 69027338, compound

Participants

Reaction Steps

Following the procedure detailed in Example 1,1,4,7,7,9-pentamethylspiro-[4.5]decan-1,2-diol was prepared by reduction of 6,6,8,10-tetramethyl-1-oxadispiro-[2.0.5.3]dodecan-12-one with lithium aluminum hydride. A solution of Dess-Martin periodinane (780 mg, 1.84 mmol) in CH2Cl2 (20 mL) was added in one dash to a stirred solution of 1,4,7,7,9-pentamethylspiro[4.5]decan-1,2-diol (400 mg, 1.66 mmol) in CH2Cl2 (15 mL). Stirring was continued at room temperature for 6 h, prior to quenching by dropwise addition of a solution of Na2S2O3 (950 mg, 6.00 mmol) in satd. aq. NaHCO3 (40 mL). After stirring for 30 min., water (50 mL) was added, the organic layer was separated, and the aqueous one extracted with CH2Cl2 (50 mL). The combined organic extracts were washed with water (50 mL), dried (Na2SO4), vacuum-filtrated over a pad of Celite®, and concentrated on the rotary evaporator. The resulting residue (430 mg) was separated by repeated silica-gel FC (pentane/Et2O, 9:1, Rf=0.48) to finally provide the weaker, less polar (1R*,4R*,5S*,9R*)-configured diastereoisomer of 1-hydroxy-1,4,7,7,9-pentamethylspiro[4.5]decan-2-one (60 mg, 15%) in pure form as colorless crystals, mp. 72-73° C.

Provenance & Evidence