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

HRID 354065

反応式

HRID 354065 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. temperaturecooled 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-10446a06760146dab4d29bc9145fdae5
出典データセット
uspto-grants-2004_06
特許番号
US06756400B2

関連ノート

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