Dimethyl Sulfoxide → HCID 53685202, compound

To a solution of oxalyl chloride (2.0M in methylene chloride, 9.60 mL, 19.2 mmol) in methylene chloride (100 mL) at −60° C. was added a solution of dimethyl sulfoxide (3.01 g, 38.6 mmol) in methylene chloride (10 mL) and the mixture was stirred for 5 min. A solution of (S)-(−)-1-(t-butoxycarbonyl)-2-pyrrolidinemethanol (3.08 g, 15.3 mmol) in methylene chloride (20 mL) was added dropwise over 5 min. After 30 min, triethylamine (12.8 mL, 91.8 mmol) was added and the reaction mixture was stirred at −60° C. for 15 min and then warmed to rt for a further 10 min. Water (50 mL) was added and the mixture extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The crude residue was dissolved in methylene chloride (100 mL) and treated with methyl (triphenylphosphoranylidene)acetate (1.4 eq). After 15 h the reaction mixture was concentrated and purified by silica gel chromatography to give the desired product (3.54 g, 90%).

1. waitAfter 30 min
2. stirringthe reaction mixture was stirred at −60° C. for 15 min
3. extractionthe mixture extracted with methylene chloride
4. dry with materialThe combined organic extracts were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. dissolutionThe crude residue was dissolved in methylene chloride (100 mL)
8. concentrationAfter 15 h the reaction mixture was concentrated
9. custompurified by silica gel chromatography

ORD record

ord-b16007f99f194dc3a7c2e55e6d610e47

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06228872B1