Stannous chloride dihydrate → HCID 24985317, compound

HRID 503941Notes

Reaction equation

HRID 503941 reaction equation
O.O.Cl[Sn]Cl.C(OC([N:13]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=3)(=[O:26])=[O:25])=[CH:20][C:19]=2[CH3:36])[CH2:14]1)=O)(C)(C)C.C([O-])(O)=O.[Na+]>C(O)(C)C>[CH3:36][C:19]1[CH:20]=[C:21]([S:24]([C:27]2[CH:28]=[CH:29][C:30]([NH2:33])=[CH:31][CH:32]=2)(=[O:26])=[O:25])[CH:22]=[CH:23][C:18]=1[CH:15]1[CH2:16][CH2:17][NH:13][CH2:14]1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 59428370HCID 59428370, compound

Product 1

HCID 24985317HCID 24985317, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
75 °C

Procedure

SnCl2.2H2O (1.74 g, 7.726 mmol) was added to a solution of 3-[2-methyl-4-(4-nitro-benzenesulfonyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.69 g, 1.545 mmol) (prepared following the procedure described in Example 3) in isopropanol (20 mL) and the mixture was stirred at 75° C. for 2 hours. The reaction mixture was then cooled to 0° C. and a saturated solution of NaHCO3 was added. The gelatinous material obtained was filtered and the solvent was evaporated under reduced pressure. The crude material was purified via flash chromatography (DCM/MeOH/NH4OH) to give 0.407 g (83% yield) of 4-(3-methyl-4-pyrrolidin-3-yl-benzenesulfonyl)-phenylamine as a white foam: MS (M+H)=317.

Workup

  1. customprepared
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. customThe gelatinous material obtained
  4. filtrationwas filtered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe crude material was purified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-8614facaed5c472ca68f4a60edafd924
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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