Hydrogen Peroxide → 1-(tert-Butyl) 2-methyl 4-(hydroxymethyl)pyrrolidine-1,2-dicarboxylate

To a solution of 4-methylene-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1g, 4.149 mmol) in THF (25 ml), 0.5 M solution of 9-BBN in THF (9.8 ml, 4.979 mmol) was added at 0° C. and stirred for 2 hrs at room temperature. The reaction mixture was cooled to 0° C., and then 2N NaOH (2.43 ml, 4.979 mmol) and 30% H2O2 (1.6 ml, 14.93 mmol) were added. The reaction mixture was stirred at room temperature for 4 hr and later it was poured into water. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, filtered and concentrated under vacuum. Purification by column chromatography offered 4-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester as a yellow oil (6 g, 56%).

1. temperatureThe reaction mixture was cooled to 0° C.
2. stirringThe reaction mixture was stirred at room temperature for 4 hr
3. extractionThe mixture was extracted with ethyl acetate
4. washThe ethyl acetate layer was washed with brine
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customPurification by column chromatography

ORD record

ord-81b0daee2a4b40e998e811f08e74448e

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08252797B2