N-carbomethoxy diallyl amine → 2,3-Dihydro-pyrrole-1-carboxylic acid methyl ester

The obtained N-carbomethoxy diallyl amine (400 g) was dissolved in 1.5 l of dichloromethane purged with nitrogen for 10 minutes by bubbling nitrogen through the stirred solution. In a 5 l flask fitted with a mechanical stirrer and an addition funnel, was charged the Grubb's catalyst (bis(tricyclohexylphosphine)styrylrutheniumdichloride (3 g, 3.9 mmol) under a steady purge. Dichloromethane was added and the resultant dark solution was stirred at r.t. with nitrogen bubbling for 10 minutes. The N-carbomethoxy diallyl amine solution was added to the catalyst solution over a period of 2 hours. When the addition was complete, the solution was stirred at r.t. for 2.5 days. Then, the reaction mixture was concentrated to an oil, which was subsequently purified by vacuum distillation. The desired product was obtained as a clear colorless liquid boiling at about 90° C. (10 mm of Hg) The NMR was consistent with the expected structure.

1. custompurged with nitrogen for 10 minutes
2. customby bubbling nitrogen through the stirred solution
3. customIn a 5 l flask fitted with a mechanical stirrer and an addition funnel
4. additionWhen the addition
5. stirringthe solution was stirred at r.t. for 2.5 days
6. concentrationThen, the reaction mixture was concentrated to an oil, which
7. distillationwas subsequently purified by vacuum distillation

ORD record

ord-eea5c107c1334067a53b6df1007d4b8f

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642642B2