Sodium Hydroxide → HCID 57543943, compound

Temperature

40 °C

To a solution of tert-butyl 2-methyl-1-oxo-1-(pyrrolidin-1-yl)propan-2-ylcarbamate (Compound F5) (2.696 g, 10.52 mmol) in THF (20 mL) was a 1M LAH in THF (42.1 mL, 42.07 mmol) solution dropwise added (over approximately 10 min) at 0° C. under a nitrogen atmosphere. The resultant mixture was stirred at rt for 1 h and heated at 40° C. over night. The reaction was cooled to 0° C. and Na2SO4×10H2O followed by NaOH (2M, 2 mL) was added. The mixture was diluted with Et2O (100 mL) and the resultant mixture was filtered. The solids were washed with Et2O (3×50 mL). To the filtrate was HCl (1.25 N aq. solution, 15 mL) in EtOH added. The filtrate was concentrated and the residue mixed with EtOH (60 mL). The EtOH was removed under reduced pressure. IPA (30 mL) was added and the mixture sonicated for 2 min. After filtration was the title compound (1.89 g, 96%) obtained as a HCl salt. 1H NMR (400 MHz, CDCl3) δ 1.00, 1.71, 2.29, 2.41, 2.63. Total no of protons: 19.

1. additiondropwise added (over approximately 10 min) at 0° C. under a nitrogen atmosphere
2. temperatureThe reaction was cooled to 0° C.
3. additionwas added
4. filtrationthe resultant mixture was filtered
5. washThe solids were washed with Et2O (3×50 mL)
6. additionadded
7. concentrationThe filtrate was concentrated
8. additionthe residue mixed with EtOH (60 mL)
9. customThe EtOH was removed under reduced pressure
10. additionIPA (30 mL) was added
11. customthe mixture sonicated for 2 min
12. filtrationAfter filtration

ORD record

ord-2f86a40231b24ec589a3789983328152

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08361998B2