Phosgene → 2,3-Dihydro-1H-pyrrolizine-5-carbonyl chloride

HRID 485367Notes

Reaction equation

HRID 485367 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH2:5]1[C:12]2[N:8]([CH:9]=[CH:10][CH:11]=2)[CH2:7][CH2:6]1>C1(C)C=CC=CC=1.CCOCC>[CH2:11]1[C:12]2[N:8]([C:7]([C:1]([Cl:4])=[O:2])=[CH:6][CH:5]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 2593612,3-dihydro-1H-pyrrolizine

Product 1

HCID 134904052,3-Dihydro-1H-pyrrolizine-5-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred, ice-bath cooled portion (30 ml) of 12.5% phosgene in toluene was added a solution of 2,3-dihydro-1H-pyrrolizine (0.80 g, 0.0074 m) in ether (30 ml) dropwise over ca two minutes. After stirring cold for ca 2.5 hr, the reaction mixture is allowed to warm to room temperature, the volatiles are removed in vacuo, and the resultant crystalline 2,3-dihydro-1H-pyrrolizine-5-carbonyl chloride used as is in the next step.

Workup

  1. customthe volatiles are removed in vacuo

Sources & evidence

ORD record
ord-c810a1ac01334986988088ce79433d35
Source dataset
uspto-grants-1985_08
Patent number
US04536512

Reaction notes

Loading…