Aluminium lithium hydride → (S)-N-(5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

HRID 473077Notes

Reaction equation

HRID 473077 reaction equation
[CH3:1][CH:2]([S:4]([NH:7][C@@H:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:17][C:18]3[CH:19]=[C:20]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=3)[C:21](OC)=[O:22])[CH:14]=2)[CH2:9]1)(=[O:6])=[O:5])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:22][CH2:21][C:20]1[CH:19]=[C:18]([CH:27]=[C:26]([C:28]([F:31])([F:29])[F:30])[CH:25]=1)[CH2:17][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C@H:8]([NH:7][S:4]([CH:2]([CH3:1])[CH3:3])(=[O:6])=[O:5])[CH2:16]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66734082(S)-methyl 3-((2-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate

Product 1

HCID 46935616(S)-N-(5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamideYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To (S)-methyl 3-((2-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate (0.044 mmol, 20 mg) at 0° C. in THF (1 mL) under an argon atmosphere was added Lithium aluminium hydride in THF (0.044 mmol, 0.044 mL) dropwise. The reaction was left to stir for 1.5 hrs at 0° C. The reaction was quenched with water before the addition of 5N HCl (aq) to adjust the pH to 5. The mixture was filtered through a celite cartridge before washing with EtOAc. The EtOAc layer was washed with water (×1) before drying the EtOAc over MgSO4. The solvent was removed in vacuo before purifying the crude (1:1 EtOAc/Heptane, 4 g silica cartridge) to give the title compound (7.5 mg, 40%). MS (ESI): m/z [M+Na]+ 450.0

Workup

  1. waitThe reaction was left
  2. customThe reaction was quenched with water before the addition of 5N HCl (aq)
  3. filtrationThe mixture was filtered through a celite cartridge
  4. washbefore washing with EtOAc
  5. washThe EtOAc layer was washed with water (×1)
  6. dry with materialbefore drying the EtOAc over MgSO4
  7. customThe solvent was removed in vacuo
  8. custombefore purifying the crude (1:1 EtOAc/Heptane, 4 g silica cartridge)

Sources & evidence

ORD record
ord-f7b132818952409089617c1aa8252965
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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