Diisobutylaluminum hydride → (S)-N-(5-((4-(hydroxymethyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

HRID 43015Notes

Reaction equation

HRID 43015 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[CH2:21][C@H:20]([NH:25][S:26]([CH:29]([CH3:31])[CH3:30])(=[O:28])=[O:27])[CH2:19]3)[C:10]=1[C:11]([F:14])([F:13])[F:12])=O)C.[H-].C([Al+]CC(C)C)C(C)C.CC(C[AlH]CC(C)C)C>C1COCC1>[OH:3][CH2:4][C:6]1[CH:7]=[N:8][N:9]([CH2:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[CH2:21][C@H:20]([NH:25][S:26]([CH:29]([CH3:31])[CH3:30])(=[O:28])=[O:27])[CH2:19]3)[C:10]=1[C:11]([F:12])([F:13])[F:14]

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 21225700DiisobutylaluminumhydrideHCID 67088081(S)-Ethyl 1-((2-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 44555729(S)-N-(5-((4-(hydroxymethyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-Ethyl-1-((2-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate (0.026 mmol, 12 mg) was dissolved in THF (1 mL) and diisobutylaluminium hydride (0.304 mmol, 50 μL, 43.3 mg) added. After 15 min an additional 100 uL of DIBAL added and stirring continued for 30 min before the reaction was quenched with methanol. The mixture was concentrated then partitioned between DCM and Water. The aq. phase was acidified with 5N HCl and the phases mixed and separated using a hydrophobic frit. The organics were concentrated to dryness to give the desired compound as a clear film (10.6 mg, 0.025 mmol, 97%). MS (ESI): m/z [M+H]+ 418.2.

Workup

  1. customwas quenched with methanol
  2. concentrationThe mixture was concentrated
  3. customthen partitioned between DCM and Water
  4. additionthe phases mixed
  5. customseparated
  6. concentrationThe organics were concentrated to dryness

Sources & evidence

ORD record
ord-86652bf3997b4a41bc59ec78da96a115
Source dataset
uspto-grants-2013_09
Patent number
US08536214B2

Reaction notes

Loading…