Sodium Sulfate → HCID 59428434, compound

HRID 503933Notes

Reaction equation

HRID 503933 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OC(=O)[CH2:13][N:14]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=3)(=[O:27])=[O:26])=[CH:21][C:20]=2[CH3:35])[CH2:15]1)(C)(C)C.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:35][C:20]1[CH:21]=[C:22]([S:25]([C:28]2[CH:29]=[C:30]([OH:34])[CH:31]=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH:23]=[CH:24][C:19]=1[CH:16]1[CH2:17][CH2:18][N:14]([CH3:13])[CH2:15]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 66877573HCID 66877573, compound

Product 1

HCID 59428434HCID 59428434, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of LAH (1.0 M in THF, 0.51 mL) was added to a solution of {3-[4-(3-hydroxy-benzenesulfonyl)-2-methyl-phenyl]-pyrrolidin-1-yl}-acetic acid tert-butyl ester (85 mg, 0.2036 mmol) in THF (1 mL). The reaction mixture was stirred at reflux for 2 hours, it was cooled to room temperature and Na2SO4. 10H2O was added. The mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified via flash chromatography (DCM/MeOH/NH4OH) to give 42 mg of 3-[3-methyl-4-(1-methyl-pyrrolidin-3-yl)-benzenesulfonyl]-phenol as a white foam: MS (M+H)=332.

Workup

  1. temperatureat reflux for 2 hours
  2. addition10H2O was added
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was purified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-592732b90d684604a02678defb4bed0a
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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