Ammonia → Methyl 1-(4-chlorophenyl)-2-(4-sulphamoylphenyl)-6,7-dihydro-5H-pyrrolizine-3-carboxylate
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24]C=C[CH:21]=3)=[C:10]3[N:14]([C:15]=2[C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][CH2:11]3)=[CH:4][CH:3]=1.Cl[S:27]([OH:30])(=O)=[O:28].[NH3:31].O.Cl[CH:34]([Cl:36])[CH3:35]>>[Cl:36][C:34]1[CH:24]=[CH:25][C:20]([C:9]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([S:27](=[O:30])(=[O:28])[NH2:31])=[CH:3][CH:4]=3)=[C:15]([C:16]([O:18][CH3:19])=[O:17])[N:14]3[C:10]=2[CH2:11][CH2:12][CH2:13]3)=[CH:21][CH:35]=1Participants
Conditions
- Temperature
- 2.5 °C
Procedure
Methyl 2-(4-chlorophenyl)-1-phenyl-6,7-dihydro-5H-pyrrolizine-3-carboxylate (4.0 g, 11.4 mmol) is dissolved in dichloroethane (40 ml), and the solution is cooled to 0-5° C. in an ice bath. A solution of chlorosulphonic acid (2.0 g, 17.3 mmol) in dichloroethane (20 ml) is slowly added dropwise to this (IT<10° C., 15 min) and the mixture is then stirred at RT for 12 h. A solution of NH3 in dichloroethane (40 ml) saturated in the cold is added, and the mixture is stirred at RT for a further 12 h. It is then treated (pH 9) with water (20 ml), and the organic phase is separated in a separating funnel. Solid insoluble in water is filtered off from the aqueous phase with suction and dried in vacuo. The dried solid substance is crystallized from MeOH: 0.76 g (product A).
Workup
- stirringthe mixture is stirred at RT for a further 12 h
- customthe organic phase is separated in a separating funnel
- filtrationSolid insoluble in water is filtered off from the aqueous phase with suction
- customdried in vacuo
- customThe dried solid substance is crystallized from MeOH
Sources & evidence
- ORD record
- ord-da3c3c4e89054c3e84f8acf6992471f9
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06936632B2
Reaction notes
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