Diisobutylaluminum hydride → HCID 59564912, compound

Temperature

-78 °C

DIBAL-H (73.65 mL, 110.5 mmol, 1.5M in toluene) was added portionwise to a solution of tert-butyl 2,2-dimethyl-5-oxopyrrolidine-1-carboxylate (23.10 g, 108.3 mmol) in dry Et2O (200 mL) cooled to −78° C. The reaction was stirred for 1 hour at −78° C. and then allowed to warm to room temperature and stirred overnight. The reaction was quenched with NH4OH (50 mL) and stirred for 20 minutes. The reaction was then diluted with EtOAc (200 mL), 0.5M Rochelle's Salt (100 mL) was added, and the layers were separated. The organic fraction was washed with 0.5M Rochelle's Salt (2×100 mL), brine (100 mL), dried (MgSO4) and concentrated to an oil. The oil was taken up in a solution of p-TsOH monohydrate (2.06 g, 10.8 mmol) in MeOH (200 mL) and stirred overnight at room temperature. The reaction was then concentrated, taken up in EtOAc (200 mL), washed with saturated Na2CO3 (2×100 mL), brine (50 mL), dried (MgSO4) and concentrated to give tert-butyl 5-methoxy-2,2-dimethylpyrrolidine-1-carboxylate (24.07 g, 96.9% yield) as an oil.

1. temperatureto warm to room temperature
2. stirringstirred overnight
3. customThe reaction was quenched with NH4OH (50 mL)
4. stirringstirred for 20 minutes
5. additionThe reaction was then diluted with EtOAc (200 mL), 0.5M Rochelle's Salt (100 mL)
6. additionwas added
7. customthe layers were separated
8. washThe organic fraction was washed with 0.5M Rochelle's Salt (2×100 mL), brine (100 mL)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated to an oil
11. stirringstirred overnight at room temperature
12. concentrationThe reaction was then concentrated
13. washwashed with saturated Na2CO3 (2×100 mL), brine (50 mL)
14. dry with materialdried (MgSO4)
15. concentrationconcentrated

ORD record

ord-c01d0be7e2114075aee0a8cfbc3fbbfc

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372842B2