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

HRID 2275527Notes

Reaction equation

HRID 2275527 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% AeOEt 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% AeOEt in hexanes

Sources & evidence

ORD record
ord-160ed556c2cc476c85d93d6fa6b126e0
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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