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

HRID 354065

Reaction equation

HRID 354065 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. 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

Sources & evidence

ORD record
ord-10446a06760146dab4d29bc9145fdae5
Source dataset
uspto-grants-2004_06
Patent number
US06756400B2

Linked notes

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