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

HRID 351150

Reaction equation

HRID 351150 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4af4207eaf724d55ac7e72631be3c989
Source dataset
uspto-grants-2007_02
Patent number
US07183323B2

Linked notes

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