Réaction #89178

Équation de réaction

2-(((2S,3R)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione

DIPEA

carbamate

hydrazine hydrate

allyl chloroformate

→

title compound

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

Solvants

CH2Cl2

MeOH

Conditions de réaction

Traitement

1. 1
   Concentrationthe reaction was concentrated
2. 2
   Autreto remove the CH2Cl2
3. 3
   Lavagewashed with 1 M HCl (2×), brine (2×)
4. 4
   Séchagedried (MgSO4)
5. 5
   Concentrationconcentrated
6. 6
   Autreto give the crude carbamate which
7. 7
   Autrewas used without further purification
8. 8
   Températurewas heated at 60° C. for 2 h
9. 9
   TempératureThe mixture was cooled to rt
10. 10
    Autrethe solvent was removed in vacuo
11. 11
    workup.DISSOLUTIONThe crude was dissolved in EtOAc
12. 12
    Lavagewashed with 2 N NaOH (2×), brine
13. 13
    Séchagedried (Na2SO4)
14. 14
    AutreThe solvent was removed in vacuo

Mode opératoire

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]+.

Source