Lithium aluminum hydride → Propane-1-sulfonic acid (2-fluoro-3-hydroxymethyl-phenyl)-amide

HRID 1397846Notes

Reaction equation

HRID 1397846 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12])[C:5]=1[F:17].[AlH4-].[Li+].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[F:17][C:5]1[C:4]([CH2:3][OH:2])=[CH:9][CH:8]=[CH:7][C:6]=1[NH:10][S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 28112Lithium aluminum hydrideHCID 62649Sodium sulfate decahydrateHCID 579632422-Fluoro-3-(propane-1-sulfonylamino)-benzoic acid methyl ester

Product 1

HCID 58087499Propane-1-sulfonic acid (2-fluoro-3-hydroxymethyl-phenyl)-amideYield 87.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-fluoro-3-(propane-1-sulfonylamino)-benzoic acid methyl ester (20, 3.80 g, 13.8 mmol) in 133 mL of tetrahydrofuran, lithium tetrahydroaluminate (1.00 M in tetrahydrofuran, 20.0 mL, 20.0 mmol) was added under an atmosphere of nitrogen at room temperature. The reaction was stirred at room temperature for 8 hours, followed by addition of 10 g of sodium sulfate decahydrate. After 12 hours, the reaction was filtered, the filtrate concentrated under vacuum and purified with silica gel column chromatography eluting with 5% methanol in dichloromethane to give the desired compound as a white solid (21, 3.0 g, 87.9%).

Workup

  1. waitAfter 12 hours
  2. filtrationthe reaction was filtered
  3. concentrationthe filtrate concentrated under vacuum
  4. custompurified with silica gel column chromatography
  5. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-e41ede936f744a73a10d687a43b3ded3
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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