Chlorosuccinimide → HCID 22335631, compound

HRID 586627Notes

Reaction equation

HRID 586627 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:14]3[N:10]([CH2:11][CH2:12][CH2:13]3)[CH:9]=2)=[CH:4][CH:3]=1.[Cl:22]N1C(=O)CCC1=O>C1COCC1>[Cl:22][C:9]1[N:10]2[C:14](=[C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH2:13][CH2:12][CH2:11]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 15390832HCID 15390832, compound

Product 1

HCID 22335631HCID 22335631, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The clear solution of 6-(4-fluorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine (Example 8 d, 2.77 g, 10 mmol) in THF (20 ml) is treated at RT with N-chlorosuccinimide (NCS, 1.34 g, 10 mmol). The solution, immediately turning from yellow to black-coloured with spontaneous heating, is stirred for a further 10 min, then adsorbed on an Al2O3 column (100 g, TSC-ICI), and the substance sought is eluted with ethyl acetate-n-hexane 1:9 (Rf=0.8, starting material Rf=0.6). The eluate fractions are concentrated in vacuo and the residue is crystallized from diisopropyl ether: 1.63 g (52%)

Workup

  1. washthe substance sought is eluted with ethyl acetate-n-hexane 1:9 (Rf=0.8, starting material Rf=0.6)
  2. concentrationThe eluate fractions are concentrated in vacuo
  3. customthe residue is crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-067d62e6be7d4063b865689fa5aaf774
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

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