Aluminium lithium hydride → (2-Benzylisoindolin-5-yl)methanol

HRID 1486511Notes

Reaction equation

HRID 1486511 reaction equation
[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17](OC)=[O:18])[CH:14]=2)[CH2:9]1)[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[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:17][OH:18])[CH:14]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 23301778Methyl 2-benzylisoindoline-5-carboxylate

Product 1

HCID 19828502(2-Benzylisoindolin-5-yl)methanolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 2-benzyl-2,3-dihydro-1H-isoindole-5-carboxylate (from above) was dissolved in anhydrous tetrahydrofuran (75 ml) and added dropwise over 15 minutes to a rapidly stirred suspension of lithium aluminium hydride (1.71 g, 45.0 mmol) in anhydrous tetrahydrofuran (75 ml). The mixture was stirred at room temperature for 2 hours whereupon excess lithium aluminium hydride was destroyed by the slow dropwise addition of 1 M sodium sulphate solution (12 ml). The solids were removed by filtration, rinsed with ethyl acetate (2×50 ml) and sucked dry. The solvent was removed in vacuo to afford (2-benzyl-2,3-dihydro-1H-isoindol-5-yl)-methanol (7.15 g, 99%) as a tan solid. 1H NMR (DMSO-d) 7.40-7.30 (4H, m), 7.28 (1H, m), 7.17-7.10 (3H, m), 5.10 (1H, t), 4.47 (2H, d), 3.85 (2H, s), 3.82 (2H, s), 3.80 (2H, s). MS: [M+H]+ 240.

Workup

  1. customwas destroyed by the slow dropwise addition of 1 M sodium sulphate solution (12 ml)
  2. customThe solids were removed by filtration
  3. washrinsed with ethyl acetate (2×50 ml)
  4. customsucked dry
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-05f114d1b3934be6b75aa0035fefb8cc
Source dataset
uspto-grants-2016_08
Patent number
US09428439B2

Reaction notes

Loading…