1-Benzyl-3-pyrrolidinone → 2-(1-benzyl-3-hydroxypyrrolidin-3-yl)-N-(tert-butyl)benzenesulfonamide

HRID 969071Notes

Reaction equation

HRID 969071 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.[CH2:20]([N:27]1[CH2:31][CH2:30][C:29](=[O:32])[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCCCC.CCOCC>[CH2:20]([N:27]1[CH2:31][CH2:30][C:29]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:6]([NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])(=[O:8])=[O:7])([OH:32])[CH2:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 698901-Benzyl-3-pyrrolidinoneHCID 314059N-(1,1-Dimethylethyl)benzenesulfonamideHCID 178418306HCID 178418306, compound

Product 1

HCID 666616262-(1-benzyl-3-hydroxypyrrolidin-3-yl)-N-(tert-butyl)benzenesulfonamideYield 39.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8003PentaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of N-(tert-butyl)benzenesulfonamide (536 mg, 0.00251 mol) in ether (10 mL, 0.1 mol) was added 1.7 M of tert-butyllithium in pentane (4.4 mL) under nitrogen at −78° C. The mixture was stirred at −78 Celsius for 15 min, then at 0 Celsius for 1 hour, and then cooled down to −78 Celsius again. A solution of 1-benzylpyrrolidin-3-one (400.0 mg, 0.002283 mol) in ether (3 mL) was added to the above solution. The reaction solution was stirred at −78 Celsius for 2 hours, then quenched with saturated NH4Cl aqueous solution, and then extracted with EtOAc. The organic phase was washed with brine, then dried over MgSO4. The residue was purified by flash chromatography on silica gel column with 30% AcOEt in hexanes to give the desired compound (350 mg, 39% yield). MS (ESI): 389.1 (M+H+).

Workup

  1. waitat 0 Celsius for 1 hour
  2. temperaturecooled down to −78 Celsius again
  3. stirringThe reaction solution was stirred at −78 Celsius for 2 hours
  4. customquenched with saturated NH4Cl aqueous solution
  5. extractionextracted with EtOAc
  6. washThe organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. customThe residue was purified by flash chromatography on silica gel column with 30% AcOEt in hexanes

Sources & evidence

ORD record
ord-e5d767029a06463581c5a697ffe78d01
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

Loading…