Dimethyl Sulfoxide → N-(tert-Butoxycarbonyl)-D-prolinal

Temperature

-78 °C

Oxalyl chloride (9.0 mL, 100 mmol) was added to a solution of DMSO (10.5 mL, 150 mmol) in 80 mL of CH2Cl2 at −78° C., under a nitrogen atmosphere. The solution was stirred for 20 min at −78° C., tert-butyl (2R)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (9.9 g, 49 mmol) was added, and the resultant solution stirred at −78° C. for 20 min. Triethylamine (28 mL, 200 mmol) was added to the reaction solution, the dry ice-acetone bath was removed, and the resultant solution was allowed to stir for two hours, slowly warming to ambient temperature. The reaction solution was quenched with brine, the phases were separated, and the organic phase was washed with 1 M KH2PO4 and saturated NaHCO3. The organic solution was then dried over Na2SO4, filtered, and concentrated to an orange oil. This oil was then dissolved in heptane, filtered through a plug of silica gel eluting with heptane, and the filtrate was concentrated to yield tert-butyl (2R)-2-formylpyrrolidine-1-carboxylate (7.87 g).

1. customthe dry ice-acetone bath was removed
2. stirringto stir for two hours
3. temperatureslowly warming to ambient temperature
4. customThe reaction solution was quenched with brine
5. customthe phases were separated
6. washthe organic phase was washed with 1 M KH2PO4 and saturated NaHCO3
7. dry with materialThe organic solution was then dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated to an orange oil
10. dissolutionThis oil was then dissolved in heptane
11. filtrationfiltered through a plug of silica gel eluting with heptane
12. concentrationthe filtrate was concentrated

ORD record

ord-2813a31ffbc947819b5df1b62d6deea1

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07727997B2