1-Benzyl-5-oxopyrrolidine-3-carboxamide → (1-Benzylpyrrolidin-3-yl)methanamine

HRID 1276360ノート

反応式

HRID 1276360 の反応式
[CH2:1]([N:8]1[C:12](=O)[CH2:11][CH:10]([C:14]([NH2:16])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:16][CH2:14][CH:10]1[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1

参加物

4

反応物 2

HCID 52217541-Benzyl-5-oxopyrrolidine-3-carboxamideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 3157467(1-Benzylpyrrolidin-3-yl)methanamine収率 77.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid amide (22 g, 0.1 mol) was added portionwise to a stirred solution of lithium aluminum hydride (9.5 g, 0.25 mol, 2.5 equiv.) in dry tetrahydrofuran (600 mL). After the initial effervescence had subsided, the reaction mixture was heated at reflux at room temperature for 24 h, at which time analysis of the reaction mixture by LCMS showed there was no starting material. The reaction mixture was quenched by dropwise addition of saturated sodium sulphate solution with stirring until no further effervescence was observed. The suspension was filtered through a celite plug, eluting with diethyl ether (200 mL). The solvent was remove to afford 3-(RS)-aminomethyl-1-benzylpyrrolidine as an oil (14.7 g) which was used directly without further purification.

後処理

  1. temperaturethe reaction mixture was heated
  2. customThe reaction mixture was quenched by dropwise addition of saturated sodium sulphate solution
  3. filtrationThe suspension was filtered through a celite plug
  4. washeluting with diethyl ether (200 mL)
  5. customThe solvent was remove

出典と根拠

ORDレコード
ord-034d0e5929f547feb8c3ecfdbd31cc90
出典データセット
uspto-grants-2000_12
特許番号
US06166015

反応ノート

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