Reaktion #89178

Reaktionsgleichung

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

Lösungsmittel

CH2Cl2

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthe reaction was concentrated
2. 2
   Sonstigeto remove the CH2Cl2
3. 3
   Waschenwashed with 1 M HCl (2×), brine (2×)
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto give the crude carbamate which
7. 7
   Sonstigewas used without further purification
8. 8
   Temperaturwas heated at 60° C. for 2 h
9. 9
   TemperaturThe mixture was cooled to rt
10. 10
    Sonstigethe solvent was removed in vacuo
11. 11
    workup.DISSOLUTIONThe crude was dissolved in EtOAc
12. 12
    Waschenwashed with 2 N NaOH (2×), brine
13. 13
    Trocknendried (Na2SO4)
14. 14
    SonstigeThe solvent was removed in vacuo

Vorschrift

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]+.

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