Ammonia → Methyl 2-(4-chlorophenyl)-1-(4-sulphamoylphenyl)-6,7-dihydro-5H-pyrrolizine-3-carboxylate

HRID 586630Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][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>ClC(Cl)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:21]=[CH:22][C:23]([S:27](=[O:30])(=[O:28])[NH2:31])=[CH:24][CH:25]=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

Participants

Conditions

Temperature: 2.5 °C

Procedure

Methyl 2-(4-chlorophenyl)-1-phenyl-6,7-dihydro-5H-pyrrolizine-3-carboxylate (0.87 g, 2.5 mmol) is dissolved in dichloroethane (10 ml) and the solution is cooled to 0-5° C. in an ice bath. A solution of chlorosulphonic acid (0.5 g, 5.7 mmol) in dichloroethane (5 ml) is slowly added dropwise (IT<10° C.), and the mixture is then stirred at RT for 12 h. A solution of NH3 in dichloroethane saturated in the cold is added, and the mixture is stirred at RT for a further 12 h. The mixture is then treated with water (20 ml), and the organic phase is separated in a separating funnel. Solid which is insoluble in water is filtered off from the aqueous phase with suction and dried in vacuo. The dried solid substance is crystallized from MeOH: 0.5 g (47%); a 2nd crystal fraction crystallized from the mother liquor in the cold: 23% (0.25 g).

Workup

stirringthe mixture is stirred at RT for a further 12 h
customthe organic phase is separated in a separating funnel
filtrationis filtered off from the aqueous phase with suction
customdried in vacuo
customThe dried solid substance is crystallized from MeOH
customa 2nd crystal fraction crystallized from the mother liquor in the cold: 23% (0.25 g)

Sources & evidence

ORD record: ord-521cf1907a0b4729b404fe6f65eb7c94
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936632B2

Reaction notes

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