Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylate → (1-Benzylpyrrolidin-3-yl)methanol

HRID 351150

反応式

HRID 351150 の反応式
[CH2:1]([N:8]1[C:12](=O)[CH2:11][CH:10]([C:14](OC)=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 98909Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 5176654(1-Benzylpyrrolidin-3-yl)methanol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

First, N-benzyl-pyrrolidine-3-methanol was prepared as follows. Methyl N-benzyl-5-oxo-pyrrolidine-3-carboxylate (11.66 g, 50 mmol) was dissolved in diethyl ether and cooled to 0° C. This solution was added to a 0° C. suspension of lithium aluminum hydride in diethyl ether under nitrogen atmosphere. After addition, the mixture was refluxed for 1 hr. and then cooled with an ice bath. To quench the reaction, sodium sulfate decahydrate was added and the mixture was stirred for 1 hr. After filtration, the filtrate was collected, and concentrated to dryness to give N-Benzyl-pyrrolidine-3-methanol. ESMS (C12H17NO): calcd. 191.13; obsd. 192–2 [M+H]+. Retention time (anal. HPLC: 10–70% MeCN/H2O over 5 min)=0.95 min.

後処理

  1. customFirst, N-benzyl-pyrrolidine-3-methanol was prepared
  2. additionThis solution was added to a 0° C.
  3. additionAfter addition
  4. temperaturethe mixture was refluxed for 1 hr
  5. temperatureand then cooled with an ice bath
  6. customTo quench
  7. customthe reaction, sodium sulfate decahydrate
  8. additionwas added
  9. filtrationAfter filtration
  10. customthe filtrate was collected
  11. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-4af4207eaf724d55ac7e72631be3c989
出典データセット
uspto-grants-2007_02
特許番号
US07183323B2

関連ノート

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