Aluminium lithium hydride → [3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-methanol

HRID 2059660Notes

Reaction equation

HRID 2059660 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)[CH:8]=[C:7]([NH2:17])[CH:6]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:17][C:7]1[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[C:9]([C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 667334833-Amino-5-(1-methyl-1H-tetrazol-5-yl)-benzoic acid ethyl ester

Product 1

HCID 22252683[3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-methanolYield 33.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-benzoic acid ethyl ester (250 mg) in THF (5 ml) at 0° C. was added pre-cooled 1M LiAlH4 solution in THF (2 ml) dropwise. This was stirred for 3 h. The reaction mixture was poured onto ice-water and extracted into EtOAc. The organic layer was separated, dried and concentrated in vacuum. Flash chromatography (100:0 to 95:5 gradient DCM:MeOH) afforded the title compound (70 mg).

Workup

  1. additionThe reaction mixture was poured onto ice-water
  2. extractionextracted into EtOAc
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-c61edbb803e14d3a958998615c3e2a70
Source dataset
uspto-grants-2012_10
Patent number
US08278302B2

Reaction notes

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