Aluminium lithium hydride → [2-(4-Isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-methanol

HRID 2385605Notes

Reaction equation

HRID 2385605 reaction equation
C[O:2][C:3]([C:5]1[CH:26]=[CH:25][C:8]2[C:9]3[N:10]=[C:11]([C:17]4[N:21]([CH:22]([CH3:24])[CH3:23])[CH:20]=[N:19][N:18]=4)[S:12][C:13]=3[CH2:14][CH2:15][O:16][C:7]=2[CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:22]([N:21]1[CH:20]=[N:19][N:18]=[C:17]1[C:11]1[S:12][C:13]2[CH2:14][CH2:15][O:16][C:7]3[CH:6]=[C:5]([CH2:3][OH:2])[CH:26]=[CH:25][C:8]=3[C:9]=2[N:10]=1)([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 582040372-(4-isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carboxylic acid methyl ester

Product 1

HCID 58204084[2-(4-Isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-methanolYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carboxylic acid methyl ester (620 mg, 1.67 mmol) in THF (12 mL) at 0° C. was added LiAlH4 (152 mg, 4.02 mmol). The reaction mixture was stirred for 4 hours at RT before being quenched with H2O (0.15 mL), 15% NaOH(aq) (0.15 mL) and H2O (0.45 mL). The precipitate was removed by filtration, washing with methanol/DCM, and then the filtrate was concentrated in vacuo to yield the title compound as an orange solid (563 mg, 98%). LCMS: RT=3.71 min, [M+H]+=343

Workup

  1. custombefore being quenched with H2O (0.15 mL), 15% NaOH(aq) (0.15 mL) and H2O (0.45 mL)
  2. customThe precipitate was removed by filtration
  3. washwashing with methanol/DCM
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1ce2ecf65a0f494793de82453c819f75
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

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