Aluminium lithium hydride → HCID 44556366, compound

HRID 42989Notes

Reaction equation

HRID 42989 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)[CH2:17][C@H:16]([NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])[CH2:15]3)[CH:10]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[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)[CH2:17][C@H:16]([NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])[CH2:15]3)[CH:10]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 67088144(S)-ethyl-1-((2-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 44556366HCID 44556366, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-ethyl-1-((2-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (1.371 mmol, 630 mg) was dissolved in tetrahydrofuran (10 mL) and the vessel purged with nitrogen. Lithium aluminium hydride (1M, 1.371 mmol, 1.371 mL) was added dropwise and the mixture stirred at room temperature for 20 min. An additional quantity of lithium aluminium hydride (1M, 1.371 mmol, 1.371 mL) was added to complete the reaction. The reaction was quenched by addition of methanol followed by water before concentration. The residue was partitioned between 1N HCl and Ethylacetate and the organic phase collected. The aqueous phase was further extracted with EtOAc (×2). Combined organics were dried and concentrated before purification on silica eluting with 2% MeOH/DCM. Desired fractions were collected and concentrated to give (S)—N-(5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide as a colourless glass. (0.505 g, 88%) MS (ESI): m/z [M+H]+ 418.5

Workup

  1. customthe vessel purged with nitrogen
  2. customthe reaction
  3. customThe reaction was quenched by addition of methanol
  4. concentrationfollowed by water before concentration
  5. customThe residue was partitioned between 1N HCl and Ethylacetate
  6. customthe organic phase collected
  7. extractionThe aqueous phase was further extracted with EtOAc (×2)
  8. customCombined organics were dried
  9. concentrationconcentrated before purification on silica eluting with 2% MeOH/DCM
  10. customDesired fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-c23c506533ca403cbf78c4147450e71b
Source dataset
uspto-grants-2013_09
Patent number
US08536214B2

Reaction notes

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