Diisobutylaluminumhydride → HCID 44555733, compound

HRID 43033Notes

Reaction equation

HRID 43033 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:28]([F:31])([F:30])[F:29])=[N:8][N:9]([CH2:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[CH:17]([NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])[CH2:16][CH2:15]3)[CH:10]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[OH:3][CH2:4][C:6]1[C:7]([C:28]([F:29])([F:31])[F:30])=[N:8][N:9]([CH2:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[CH:17]([NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])[CH2:16][CH2:15]3)[CH:10]=1

Participants

4

Reactant 2

HCID 21225700Diisobutylaluminumhydride2×HCID 67088245Ethyl 1-((1-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 44555733HCID 44555733, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl-1-((1-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoro methyl)-1H-pyrazole-4-carboxylate (0.196 mmol, 90 mg) was dissolved in THF (5 mL) and cooled in an ice bath under nitrogen. Di-isobutyl aluminium hydride (0.588 mmol, 0.588 mL) was added dropwise and the reaction stirred for 1.5 h. The reaction mixture was warmed to room temperature and stirred for a further 30 min before an additional 0.2 ml of di-isobutyl aluminium hydride was added and stirring continued for 30 min before quenching with MeOH followed by water. The mixture was concentrated before partitioning between EtOAc/water. The aq. layer was acidified with 5N HCl until all solids were in solution. The organic phase was collected, dried and concentrated and the residue purified by HPLC to give a colourless oil which crystallised on standing (63 mg, 0.151 mmol, 77%). 1H NMR (400 MHz, CDCl3) δ 1.43 (d, 6H) 1.95 (m, 1H) 2.65 (m, 1H) 2.80 (m, 1H) 3.00 (m, 1H), 3.24 (m, 1H) 4.20 (d, 1H) 4.65 (s, 2H) 4.95 (q, 1H) 5.28 (s, 2H) 7.13 (m, 2H) 7.44 (m, 2H).

Workup

  1. temperaturecooled in an ice bath under nitrogen
  2. additionwas added
  3. stirringstirring
  4. waitcontinued for 30 min
  5. custombefore quenching with MeOH
  6. concentrationThe mixture was concentrated
  7. custombefore partitioning between EtOAc/water
  8. customThe organic phase was collected
  9. customdried
  10. concentrationconcentrated
  11. customthe residue purified by HPLC
  12. customto give a colourless oil which
  13. customcrystallised

Sources & evidence

ORD record
ord-083afb9b493048899feed4c27e04c2c3
Source dataset
uspto-grants-2013_09
Patent number
US08536214B2

Reaction notes

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