Aluminium lithium hydride → 2-Phenyl-3-(pyrrolidin-1-yl)propan-1-ol

HRID 645481Notes

Reaction equation

HRID 645481 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH2:8][CH:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=O>C1COCC1>[C:17]1([CH:9]([CH2:10][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:8][OH:7])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 687069803-Hydroxy-2-phenyl-1-pyrrolidin-1-yl propan-1-one

Product 1

HCID 448908602-Phenyl-3-(pyrrolidin-1-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of LAH (10 mmol) in THF (50 mL) is added 3-hydroxy-2-phenyl-1-pyrrolidin-1-yl propan-1-one (5 mmol) at 0° C. The reaction mixture is stirred at 0° C. for 1.5 h. After cooled down to 0° C., the reaction is quenched by the addition of Na2SO4-10H2O. The resulting mixture is filtered through celite, and the filtrate is concentrated in vacuo to give 2-phenyl-3-pyrrolidin-1-yl propan-1-ol, which is directly used for the next reaction without further purification.

Workup

  1. temperatureAfter cooled down to 0° C.
  2. customthe reaction is quenched by the addition of Na2SO4-10H2O
  3. filtrationThe resulting mixture is filtered through celite
  4. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-c28a3fc2552e4d2497e7dddb11f368e8
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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