Tosylmethyl isocyanide → 5-Methyl-6,7-dihydro-2H-pyrrolo[3,4-c]pyridin-4(5H)-one

Temperature

-78 °C

To a stirred solution of lithium bis(trimethylsilyl)amide (11 mL of 1 M solution in THF) cooled to −78° C. under nitrogen was added dropwise a solution of tosylmethyl isocyanide (1.9 g, 10 mmol) in THF (45 mL). After stirring for 40 minutes at −78° C., a solution of 1-methyl-5,6-dihydro-1H-pyridin-2-one (1.1 g, 10 mmol) in THF (10 mL) was added and the mixture was stirred at room temperature for overnight. The reaction was concentrated and the residue was partitioned between water (150 mL) and dichloromethane (150 mL). The aqueous was extracted with dichloromethane (3×). The combined organic layers were concentrated and dried under high vacuum. The resulting foam was recrystallized from dichloromethane to give 633 mg (42%) of 5-methyl-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one as a light yellow solid.

1. stirringthe mixture was stirred at room temperature for overnight
2. concentrationThe reaction was concentrated
3. customthe residue was partitioned between water (150 mL) and dichloromethane (150 mL)
4. extractionThe aqueous was extracted with dichloromethane (3×)
5. concentrationThe combined organic layers were concentrated
6. customdried under high vacuum
7. customThe resulting foam was recrystallized from dichloromethane

ORD record

ord-d5fd8ff73d5740f19c1b31700dc94f0e

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06465507B2