Potassium Carbonate → (S)-2-{(3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-indene-3-yl}propanal

Temperature

15 °C

Under a nitrogen atmosphere, a solution of (1R,3aR,4S,7aR)-octahydro-1-{(S)-1-hydroxypropane-2-yl}-7a-methyl-1H-indene-4-ol (Compound 14: 2.05 g, 9.659 mmol) synthesized according to the method described in J. Org. Chem. 1986, 51, 1264-1269, 4-acetamide-2,2,6,6-tetramethyl-1-piperidinyloxy free radical (155 mg, 0.7244 mmol) and tetra-n-butylammonium chloride (134 mg, 0.4830 mmol) in methylene chloride (90 ml) was cooled in an ice bath, and 0.5 M sodium hydrogen carbonate (45 ml) and 0.05 M potassium carbonate (45 ml) were added thereto. N-chlorosuccinimide (3.87 g, 28.98 mmol) was added thereto over 10 minutes. The reaction solution was stirred in the ice bath for 1.5 hours, at 10° C. to 18° C. for 4.5 hours, at 5° C. for 11.5 hours, and then at 10° C. to 15° C. for 4.25 hours. After adding saturated aqueous sodium thiosulfate solution (15 ml), the resulting mixture was stirred at 15° C. for 20 minutes. The resulting mixture was extracted 3 times with methylene chloride. The combined organic layer was dried over sodium sulfate, and evaporated under reduced pressure. The crude product (2.90 g) was purified by flash column chromatography to obtain (S)-2-{(3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-indene-3-yl}propanal (1.87 g).

1. waitat 10° C. to 15° C. for 4.25 hours
2. extractionThe resulting mixture was extracted 3 times with methylene chloride
3. dry with materialThe combined organic layer was dried over sodium sulfate
4. customevaporated under reduced pressure
5. customThe crude product (2.90 g) was purified by flash column chromatography

ORD record

ord-e104301ca4b24cd9824cbca90c8b171e

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173824B2