tert-Butyl ((1-benzylpyrrolidin-3-yl)methyl)carbamate → 1-(1-benzylpyrrolidin-3-yl)-N-methylmethanamine

HRID 1295870ノート

反応式

HRID 1295870 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:12](=O)[NH:13][CH2:14][CH:15]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16]1)(C)(C)C>C1COCC1>[CH2:20]([N:17]1[CH2:18][CH2:19][CH:15]([CH2:14][NH:13][CH3:12])[CH2:16]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

4

反応物 2

HCID 5108694tert-Butyl ((1-benzylpyrrolidin-3-yl)methyl)carbamateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 46608321-(1-benzylpyrrolidin-3-yl)-N-methylmethanamine収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-5 °C

実験手順

To a cooled (−5° C.) and stirred solution of LAH (1 M, 7.6 ml) in dry THF (75 ml) was added a solution of (1-benzyl-pyrrolidin-3-ylmethyl)-carbamic acid tert-butyl ester (1.47 g, 5.06 mmol) in THF (22 ml) over 20 minutes. The mixture was then heated at reflux for 2.5 hrs and cooled to room temperature and quenched by successive addition of ethyl acetate (50 ml). The organic layer was then washed with water (2×), 10% NaOH and brine, dried and evaporated to give the desired product in 90% yield.

後処理

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 2.5 hrs
  3. temperaturecooled to room temperature
  4. customquenched by successive addition of ethyl acetate (50 ml)
  5. washThe organic layer was then washed with water (2×), 10% NaOH and brine
  6. customdried
  7. customevaporated

出典と根拠

ORDレコード
ord-26bde80f474c4806bddca5de0ac9e020
出典データセット
uspto-grants-2007_07
特許番号
US07244758B2

反応ノート

読み込み中…