Aluminium lithium hydride → HCID 18405677, compound

HRID 1018373Notes

Reaction equation

HRID 1018373 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[N:13]=[C:14]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[N:15]([CH3:29])[C:16]=1[CH2:17][CH2:18][C:19]12[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2)=O)C>C1COCC1>[C:19]12([CH2:18][CH2:17][C:16]3[N:15]([CH3:29])[C:14]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[CH3:36])=[N:13][C:12]=3[CH2:10][OH:9])[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54339100HCID 54339100, compound

Product 1

HCID 18405677HCID 18405677, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (355 mg, 9.34 mmol) was added in small portions to an ice cooled solution of 5-(2-adamantan-1-yl-ethyl)-1-methyl-2-o-tolyl-1H-imidazole-4-carboxylic acid ethyl ester (Example 73, step a) (1.83 g, 4.67 mmol) in THF (20 ml). The suspension was allowed to warm to room temperature and stirred for 2 h. The reaction mixture was quenched sequentially with water (360 μl ), sodium hydroxide (2M, 360 μl) and water (3×360 μl), diluted with ethyl acetate (50 ml) and treated with magnesium sulfate. The suspension was filtered through celite, the solid residues were washed with ethyl acetate (20 ml) and chloroform (100 ml) and the filtrate was evaporated to afford white solid (2.15 g). 1H NMR (300 MHz, d6-DMSO/D2O) 7.34-7.24 (4H, m), 4.60 (2H, s), 3.32 (3H, s), 2.61 (2H, m), 2.40 (1H, br s), 2.20 (3H, s), 2.01 (3H, br s), 1.78-1.58 (12H, m), 1.32 (2H, m).

Workup

  1. customThe reaction mixture was quenched sequentially with water (360 μl ), sodium hydroxide (2M, 360 μl) and water (3×360 μl)
  2. additiondiluted with ethyl acetate (50 ml)
  3. additiontreated with magnesium sulfate
  4. filtrationThe suspension was filtered through celite
  5. washthe solid residues were washed with ethyl acetate (20 ml) and chloroform (100 ml)
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-339e2a82a01c45969ba953249ad1113a
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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