Lithium triethylborohydride → (2S,3S)-3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethyl-2-methylpyrrolidine-1-carboxylic Acid Tert-Butyl Ester

Temperature

-78 °C

To compound 3B (0.519 g, 1.39 mmol) in THF (10 mL) at −78° C. was added a 1 M solution of Super-Hydride® in THF (9.73 mL, 9.73 mmol). The cold bath was removed and the reaction was stirred for 2.5 days. The reaction was cooled to −78° C., additional 1 M Super-Hydride® in THF (4.00 mL, 4.00 mmol) was added, and reaction was stirred overnight at rt. The reaction was poured into a 1-L Erlenmeyer flask and was carefully quenched with ice while stirring and then diluted with EtOAc. The layers were separated and the organic layer washed with 1 M H3PO4, saturated aqueous NaHCO3 and brine, dried (MgSO4), filtered and concentrated. The residue was purified via flash chromatography eluting with 20-50% EtOAc/hexane to obtain compound 3C (117 mg) as a clear oil.

1. customThe cold bath was removed
2. customreaction
3. stirringwas stirred overnight at rt
4. customwas carefully quenched with ice
5. stirringwhile stirring
6. additiondiluted with EtOAc
7. customThe layers were separated
8. washthe organic layer washed with 1 M H3PO4, saturated aqueous NaHCO3 and brine
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated
12. customThe residue was purified via flash chromatography
13. washeluting with 20-50% EtOAc/hexane

ORD record

ord-2888daab477d46f59e33ee4ba8838d5d

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07625923B2