Methyl iodide → HCID 22335621, compound

HRID 586618Notes

Reaction equation

HRID 586618 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[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.[O-]S([O-])=O.[Na+].[Na+].[C:36]([O-])([O-])=O.[Na+].[Na+].CI>O.C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:36])(=[O:28])=[O:27])=[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

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 22335654HCID 22335654, compound

Product 1

HCID 22335621HCID 22335621, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-[2-(4-Fluorophenyl)-3-methoxycarbonyl-6,7-dihydro-5H-pyrrolizin-1-yl]benzenesulphonyl chloride (1.7 g, 3.8 mmol), suspended in water (10 ml), is treated with Na2SO3 (0.56 g, 4.4 mmol) and then with Na2CO3 (0.72 g, 6.8 mmol) and stirred at 70° C. for 2 h. The solution is treated with a solution of CH3I (0.88 g, 6.2 mmol) in ethanol (20 ml) and heated under reflux for 2 h. After cooling, the ethanol is removed in vacuo, the residue is treated with water (25 ml) and the product from the reaction is taken up in ethyl acetate (2×30 ml). The ethyl acetate phase is washed with conc. NaCl solution and water, dried using Na2SO4 sicc. and the filtrate is concentrated. After removing the solvent in vacuo, 0.4 g (25%) of methyl 2-(4-fluorophenyl)-1-(4-methylsulphonylphenyl)-6,7-dihydro-5H-pyrrolizine-3-carboxylate remains as a residue having a concentration of 77%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. customthe ethanol is removed in vacuo
  5. additionthe residue is treated with water (25 ml)
  6. washThe ethyl acetate phase is washed with conc. NaCl solution and water
  7. customdried
  8. concentrationand the filtrate is concentrated
  9. customAfter removing the solvent in vacuo, 0.4 g (25%) of methyl 2-(4-fluorophenyl)-1-(4-methylsulphonylphenyl)-6,7-dihydro-5H-pyrrolizine-3-carboxylate

Sources & evidence

ORD record
ord-04359f5ee2b845d18ccd6d678a0016e2
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

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