Aluminium lithium hydride → (1-Benzylpyrrolidine-2,5-diyl)dimethanol

HRID 1860377Notes

Reaction equation

HRID 1860377 reaction equation
[CH2:1]([N:8]1[CH:12]([C:13]([O-])=[O:14])[CH2:11][CH2:10][CH:9]1[C:16](OCC)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:8]1[CH:12]([CH2:13][OH:14])[CH2:11][CH2:10][CH:9]1[CH2:16][OH:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86585275HCID 86585275, compound

Product 1

HCID 11206806(1-Benzylpyrrolidine-2,5-diyl)dimethanolYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 96.4 grams of 1-benzyl-pyrrolidine-2,5-dicarboxylic acid, 2-ethyl ester, 5-methyl ester in 380 ml of anhydrous tetrahydrofuran is dripped rapidly into a solution of lithium aluminum hydride (437 mmol) in tetrahydrofuran (1.4 liter) at 0° C. After complete addition, the mixture is stirred for 3 hours at ambient temperature and then carefully quenched with 57.8 ml of water followed by 38.6 ml of 10% sodium hydroxide. The mixture is stirred overnight, filtered through Celite, the Celite washed with CH2Cl2 and the combined filtrate evaporated to provide 67.11 grams of crude (1-benzyl-5-hydroxymethyl-pyrrolidine-2-yl)-methanol.

Workup

  1. additionAfter complete addition
  2. customcarefully quenched with 57.8 ml of water
  3. stirringThe mixture is stirred overnight
  4. filtrationfiltered through Celite
  5. washthe Celite washed with CH2Cl2
  6. customthe combined filtrate evaporated

Sources & evidence

ORD record
ord-c4672a94688a473591a5afcef2511e69
Source dataset
uspto-grants-2003_03
Patent number
US06531468B2

Reaction notes

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