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

HRID 351150

반응식

HRID 351150 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4af4207eaf724d55ac7e72631be3c989
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183323B2

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