Diisobutylaluminum hydride → HCID 58204525, compound

HRID 2044306Notes

Reaction equation

HRID 2044306 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:17][CH2:16][CH2:15][C:14]3[N:10]([N:11]=[C:12]([C:18]4[N:19]([CH2:23][C:24]([F:27])([F:26])[F:25])[N:20]=[CH:21][N:22]=4)[CH:13]=3)[C:9]=2[CH:28]=1)=O.CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1.CO>[F:26][C:24]([F:25])([F:27])[CH2:23][N:19]1[C:18]([C:12]2[CH:13]=[C:14]3[N:10]([N:11]=2)[C:9]2[CH:28]=[C:5]([CH2:3][OH:2])[CH:6]=[CH:7][C:8]=2[O:17][CH2:16][CH2:15]3)=[N:22][CH:21]=[N:20]1

Participants

6

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 58204544HCID 58204544, compound

Product 1

HCID 58204525HCID 58204525, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-9-carboxylic acid methyl ester (393 mg, 1 mmol) in THF (10 mL) at −70° C. was added DIBAL (3 mL, 1 M solution in toluene, 3 mmol) and the reaction mixture stirred at 0° C. for 1 h. The reaction mixture was diluted with methanol (5 mL), then with saturated aqueous sodium potassium tartrate solution. The resultant mixture was extracted with ethyl acetate (3×20 mL), then the combined organic fractions dried (MgSO4) and concentrated in vacuo to give the title compound (370 mg, 100%).

Workup

  1. extractionThe resultant mixture was extracted with ethyl acetate (3×20 mL)
  2. dry with materialthe combined organic fractions dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75ce7fed5da74324b881a0cd73dcc71f
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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