Aluminium lithium hydride → 2-[1-Benzyl-3-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulen-6-yl]-ethanol

HRID 749805Notes

Reaction equation

HRID 749805 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]1[CH2:14][CH2:13][C:12]2[N:11]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:10]=[C:9]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[C:8]=2[CH2:7][CH2:6]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:15]([N:11]1[C:12]2[CH2:13][CH2:14][N:5]([CH2:4][CH2:3][OH:2])[CH2:6][CH2:7][C:8]=2[C:9]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[N:10]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59752513HCID 59752513, compound

Product 1

HCID 597526802-[1-Benzyl-3-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulen-6-yl]-ethanolYield 33.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [1-benzyl-3-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulen-6-yl]-acetic acid methyl ester (Example 170, 16 mg) in THF (1 mL) was added lithium aluminum hydride (100 mg). The mixture was stirred at RT for 16 h. The reaction was quenched by the addition of H2O (0.1 mL). Concentration and purification (SiO2, 2 M NH3 in MeOH/CH2Cl2) provided the title compound (5 mg). MS (ESI): exact mass calculated for C22H24ClN3O, 381.16; found, m/z 382.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.50-7.20 (m, 7H), 7.04 (d, J=7.2 Hz, 1H), 5.29 (s, 2H), 3.07-3.04 (m, 2H), 2.89-2.77 (m, 10H).

Workup

  1. customThe reaction was quenched by the addition of H2O (0.1 mL)
  2. concentrationConcentration and purification (SiO2, 2 M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-91760e5d228b4424b869364b0cef3330
Source dataset
uspto-grants-2008_07
Patent number
US07402680B2

Reaction notes

Loading…