4-Methylmorpholine → Benzyl 2-carbamoylpyrrolidine-1-carboxylate

Temperatur

0 °C

Pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (30.0 g, 121 mmol) was dissolved in DCM (180 mL). The solution was cooled to 0° C. and N-methyl-morpholine (12.8 g, 127 mmol) was added over a period of 10 mins. The solution was then cooled to −15° C. and the ethyl chloroformate (13.7 g, 126 mmol) in DCM (30 mL) was added dropwise. The solution was then stirred for 2 hours at −25° C. Next, the solution was placed under NH3 (g) while maintaining the temperature below −20° C. The reaction mixture was then stirred for 1 hour while allowing the temperature to return to 0° C. The solution was poured in H2O (120 mL) and the organic layer was partitioned from the aqueous layer. The organic layer was then washed with 1N HCl (2×50 mL), 1N NaHCO3 (2×50 mL), dried over MgSO4 and concentrated under vacuo to afford 27.8 g (88%) of 2-carbamoyl-pyrrolidine-1-carboxylic acid benzyl ester, as a colorless oil.

1. temperatureThe solution was then cooled to −15° C.
2. temperaturewhile maintaining the temperature below −20° C
3. stirringThe reaction mixture was then stirred for 1 hour
4. customto return to 0° C
5. customthe organic layer was partitioned from the aqueous layer
6. washThe organic layer was then washed with 1N HCl (2×50 mL), 1N NaHCO3 (2×50 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated under vacuo

ORD-Eintrag

ord-f289272eebc446b2ae950940d83e42bc

Quelldatensatz

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07825256B2