Aluminium lithium hydride → (1-Benzyl-3-methoxymethylpyrrolidin-3-yl)methanol

HRID 10357

Reaction equation

HRID 10357 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:18][O:19]C)[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:11]([N:8]1[CH2:9][CH2:10][C:6]([CH2:18][OH:19])([CH2:4][O:3][CH3:1])[CH2:7]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 690697751-Benzyl-3-methoxymethylpyrrolidine-3-carboxylic acid ethyl ester

Product 1

HCID 21979083(1-Benzyl-3-methoxymethylpyrrolidin-3-yl)methanolYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-benzyl-3-methoxymethylpyrrolidine-3-carboxylic acid ethyl ester (Example A18a, 2.30 g, 8.3 mmol) in anhydrous tetrahydrofuran (10 mL) is added dropwise to an ice-cold suspension of lithium aluminum hydride (0.821 g, 22 mmol) in tetrahydrofuran (50 mL). The resulting mixture is stirred at room temperature for 18 hours, cooled and quenched by the sequential dropwise addition of 1N sodium hydroxide and water. The solids are removed by filtration, re-suspended in hot tetrahydrofuran and filtered. The combined filtrates are concentrated in vacuo and the residue is partitioned between dichloromethane and water. The organic extracts are dried over Na2SO4, filtered and concentrated under vacuum to afford the title compound (1.71 g). 1N NMR (200 MHz, CDCl3): δ 7.41–7.17 (m, 5H), 3.84–3.43 (m, 4H), 3.34 (s, 2H), 3.32 (s, 3H), 2.85–2.60 (m, 2H), 2.54–2.14 (m, 3H), 1.98–1.50 (m, 2H).

Workup

  1. temperaturecooled
  2. customquenched by the sequential dropwise addition of 1N sodium hydroxide and water
  3. customThe solids are removed by filtration
  4. filtrationfiltered
  5. concentrationThe combined filtrates are concentrated in vacuo
  6. customthe residue is partitioned between dichloromethane and water
  7. dry with materialThe organic extracts are dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e346e5323871419b8510bb1982209d01
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Linked notes

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