Carbamate → (2S,3R)-Allyl 2-(aminomethyl)-3-methylpiperidine-1-carboxylate

To a solution of 2-(((2S,3R)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione (5 g, 19.4 mmol) in CH2Cl2 at 0° C. was added DIPEA (3.8 mL), followed by allyl chloroformate (2.6 mL). The reaction was allowed to warm to rt overnight. After 16 h, the reaction was concentrated to remove the CH2Cl2, and then re-suspended in EtOAc and washed with 1 M HCl (2×), brine (2×), dried (MgSO4) and concentrated to give the crude carbamate which was used without further purification. A mixture of the crude carbamate and hydrazine hydrate (2 g, 39 mmol) in MeOH (100 mL) was heated at 60° C. for 2 h. The mixture was cooled to rt and the solvent was removed in vacuo. The crude was dissolved in EtOAc and washed with 2 N NaOH (2×), brine, and then dried (Na2SO4). The solvent was removed in vacuo to obtain the title compound which was used without further purification. ESI-MS (m/z): 213 [M+1]+.

1. concentrationthe reaction was concentrated
2. customto remove the CH2Cl2
3. washwashed with 1 M HCl (2×), brine (2×)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customto give the crude carbamate which
7. customwas used without further purification
8. temperaturewas heated at 60° C. for 2 h
9. temperatureThe mixture was cooled to rt
10. customthe solvent was removed in vacuo
11. dissolutionThe crude was dissolved in EtOAc
12. washwashed with 2 N NaOH (2×), brine
13. dry with materialdried (Na2SO4)
14. customThe solvent was removed in vacuo

ORD record

ord-fbf016bb74e441ada4a45e7d402b144f

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09440982B2