1-Benzyl-3-pyrrolidinone → HCID 66661626、化合物

HRID 504273ノート

反応式

HRID 504273 の反応式
[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

参加物

6

反応物 3

HCID 698901-Benzyl-3-pyrrolidinoneHCID 314059N-(1,1-Dimethylethyl)benzenesulfonamideHCID 178418306HCID 178418306、化合物

生成物 1

HCID 66661626HCID 66661626、化合物収率 39.5%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8003Pentane溶媒

反応条件

温度
-78 °C

実験手順

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+

後処理

  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

出典と根拠

ORDレコード
ord-38a87060dc734d9e96bdeea77f1db806
出典データセット
uspto-grants-2010_08
特許番号
US07776874B2

反応ノート

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