Ammonia → HCID 10177328, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:10](C(OC(C)(C)C)=O)[N:11]3[C:15]=2[CH2:14][CH2:13][CH2:12]3)=[CH:4][CH:3]=1.Cl[S:30]([OH:33])(=O)=[O:31].[NH3:34]>C(Cl)(Cl)Cl.ClC(Cl)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:23]3[CH:28]=[CH:27][C:26]([S:30]([NH2:34])(=[O:33])=[O:31])=[CH:25][CH:24]=3)=[CH:10][N:11]3[C:15]=2[CH2:14][CH2:13][CH2:12]3)=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 2.5 °C
Procedure
tert-Butyl 1-(4-chlorophenyl)-2-phenyl-6,7-dihydro-5H-pyrrolizine-3-carboxylate (190 mg, 0.5 mmol) is taken up in CHCl3 (10 ml), the solution is cooled to 0-5° C. in an ice bath, and a solution of chlorosulphonic acid (1 ml, 1.75 g, 15 mmol) in CHCl3 (20 ml) is then slowly added dropwise (IT<10° C., 15 min). 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 it is stirred at RT for a further 12 h. It is then treated with ice water (5 ml), and the phase mixture is sucked through a G3 frit. The CHCl3 phase is separated from the now clear aqueous phase in a separating funnel. The filter residue is washed with a little water and CHCl3 and dried in vacuo. The dried solid substance is crystallized from MeOH: 0.13 g (70%).
Workup
- stirringit is stirred at RT for a further 12 h
- customThe CHCl3 phase is separated from the now clear aqueous phase in a separating funnel
- washThe filter residue is washed with a little water and CHCl3
- customdried in vacuo
- customThe dried solid substance is crystallized from MeOH
Sources & evidence
- ORD record
- ord-8e72bbf8f2bf4530ad86b01fb7fd1283
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06936632B2
Reaction notes
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