Dimethyl Sulfoxide → HCID 11357212, compound

Under N2 atmosphere with rigorous exclusion of moisture, a solution of dimethyl sulfoxide (340 mg, 4.40 mmol) in CH2Cl2 (1 mL) was injected via syringe at −70° C. within 5 min. into a stirred oxalyl chloride solution in CH2Cl2 (2 M, 1.10 ml, 2.20 mmol) diluted with CH2Cl2 (5 mL). After stirring at this temp. for 5 min., (1R*,2S*,4R*)-1,4,7,7,9,9-hexamethylspiro[4.5]decan-1,2-diol (510 mg, 2.00 mmol) dissolved in CH2Cl2 (1 mL) was injected during 5 min dropwise via syringe. Stirring was continued at −70° C. for 30 min., prior to injection of Et3N (1.01 g, 10.0 mmol). The cooling bath was removed, and the reaction mixture allowed to warm to room temp., prior to pouring into water (50 mL). The organic layer was separated, the aqueous one extracted with CH2Cl2 (2×50 mL). The combined organic extracts were washed with water (50 mL), dried (Na2SO4), and concentrated on the rotary evaporator. Purification of the resulting residue by two silica-gel FC (pentane/Et2O, 19:1, Rf=0.17) furnished (1R*,4R*)-1-hydroxy-1,4,7,7,9,9-hexamethylspiro[4.5]decan-2-one (330 mg, 65%).

1. waitwas injected during 5 min dropwise via syringe
2. stirringStirring
3. waitwas continued at −70° C. for 30 min.
4. customThe cooling bath was removed
5. temperatureto warm to room temp.
6. additionto pouring into water (50 mL)
7. customThe organic layer was separated
8. extractionthe aqueous one extracted with CH2Cl2 (2×50 mL)
9. washThe combined organic extracts were washed with water (50 mL)
10. dry with materialdried (Na2SO4)
11. concentrationconcentrated on the rotary evaporator
12. customPurification of the resulting residue by two silica-gel FC (pentane/Et2O, 19:1, Rf=0.17)

ORD record

ord-3fcf0a024f004d54817bceac19bd047b

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07632791B2