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

HRID 1639589Notes

Reaction equation

HRID 1639589 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+]>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

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 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 (16, 3.80 g, 13.8 mmol) in 133 mL of tetrahydrofuran, lithium tetrahydroaluminate (20.0 mL, 1.00 M in tetrahydrofuran, 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 NaSO4.10H2O. 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. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a white solid (17, 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
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9a7ecb2ee6144e6fbee0914035cac51d
Source dataset
uspto-grants-2012_02
Patent number
US08110576B2

Reaction notes

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