Water → HCID 67751591, compound

HRID 2210686Notes

Reaction equation

HRID 2210686 reaction equation
[C:1]1([CH:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:8]2[C@@H:12]([O:13][CH2:14][C:15]3[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=3)[CH2:11][CH2:10][N:9]2[C:23](OCC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:28]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C@H:8]2[C@@H:12]([O:13][CH2:14][C:15]3[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=3)[CH2:11][CH2:10][N:9]2[CH3:23])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67751544HCID 67751544, compound

Product 1

HCID 67751591HCID 67751591, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cis-2-(diphenylmethyl)-3-(3,5-dimethylbenzyloxy)-1-ethoxycarbonylpyrrolidine (Example 1e, 0.500 g, 1.1 mmol) in tetrahydrofuran (5.0 ml) was added 1.0M lithium aluminium hydride (5.0 ml, 5.0 mmol) and then the solution heated at reflux for 1 h. To the cooled solution was carefully added water (2 ml), 4M sodium hydroxide (2 ml) and water (4 ml) followed by ethyl acetate. The suspension was filtered through Celite and the filtrate was washed with saturated brine and dried (MgSO4). Removal of the solvent in vacuo gave cis-2-(diphenylmethyl)-3-(3,5-dimethylbenzyloxy)-1-methylpyrrolidine, as an oil. 1H NMR (360 MHz, CDCl3) δ7.05-7.43 (10H, m), 6.85 (1H, s), 6.68 (2H, s), 4.30 (1H, d, J=15.0 Hz), 4.01 (1H, d, J=16.0 Hz), 3.77 (1H, m), 3.63 (1 H, d, J=16.0 Hz), 3.24 (2H, m), 2.30 (1H, m), 2.26 (6H, s), 1.91 (5H, m).

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 1 h
  3. filtrationThe suspension was filtered through Celite
  4. washthe filtrate was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-3e87cae6e5124e28a1d437302b10ccca
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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