Potassium Carbonate → HCID 17756388, compound
Reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:3]=1[O:4][CH2:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][NH:7]1.Cl[Sn]Cl.[C:21]([O-])([O-])=O.[K+].[K+]>CCO>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:3]=1[O:4][CH2:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[CH3:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
(S)-2-(2-Chloro-5-nitro-phenoxymethyl)-pyrrolidine (3.42 g, 12.63 mmol) and SnCl2 (7.19 g, 37.9 mmol) in 45 mL EtOH were heated at 75° C. for 11 h. The reaction was treated with about 15 mL 1 N K2CO3 (aq) and stirred 40 min. The suspension was filtered through Celite and concentrated down to aqueous, which was then diluted with EtOAc and 1 N NaOH (aq). The layers were separated, and the organic layer was washed twice with 1 N NaOH and once with mix of brine and 1 N NaOH. The aqueous layers were extracted twice with fresh EtOAc. The combined organic layers were dried over sodium sulfate, filtered, and concentrated down to dryness to yield the title compound as a brown solid.