HCID 25129174, compound → tert-Butyl methyl((3R)-pyrrolidin-3-yl)carbamate

Temperature

60 °C

To a solution of Example 1E (285 mg, 0.98 mmol) in 4.4% HCO2H/MeOH (20 mL) under a nitrogen atmosphere was added Pd(OH)2 on carbon (20%, 40 mg), and the resulting mixture was heated at 60° C. for 16 hours. The mixture was cooled to room temperature and filtered through a layer of diatomaceous earth, the filter pad was washed with extra MeOH (30 mL), and the filtrate was concentrated under reduced pressure. The residue was diluted with CH2Cl2 (30 mL) and washed with 1 M NaOH, then the organic solution was dried (MgSO4), filtered, and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CD3OD) δ 4.57 (d, J=6 Hz, 1H), 3.03 (m, 2H), 2.87 (m, 1H), 2.79 (s, 3H), 2.76 (m, 1H), 1.99 (m, 1H), 1.79 (m, 1H), 1.46 (s, 9H). MS (DCI+) m/z 201 (M+H).

1. temperatureThe mixture was cooled to room temperature
2. filtrationfiltered through a layer of diatomaceous earth
3. washthe filter pad was washed with extra MeOH (30 mL)
4. concentrationthe filtrate was concentrated under reduced pressure
5. additionThe residue was diluted with CH2Cl2 (30 mL)
6. washwashed with 1 M NaOH
7. dry with materialthe organic solution was dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-37f8adb80eb846d3b130d4bbbb32948f

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278313B2