Lithium aluminum hydride → N-(2-fluoro-3-hydroxymethyl-phenyl)-4-trifluoromethyl-benzenesulfonamide

HRID 1639596Notes

Reaction equation

HRID 1639596 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:5]=1[F:24].[AlH4-].[Li+]>O1CCCC1>[F:24][C:5]1[C:4]([CH2:3][OH:2])=[CH:9][CH:8]=[CH:7][C:6]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][CH:15]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 579633152-Fluoro-3-(4-trifluoromethyl-benzenesulfonylamino)-benzoic acid methyl ester

Product 1

HCID 57963251N-(2-fluoro-3-hydroxymethyl-phenyl)-4-trifluoromethyl-benzenesulfonamideYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-fluoro-3-(4-trifluoromethyl-benzenesulfonylamino)-benzoic acid methyl ester (24, 3.34 g, 8.85 mmol) in 71 mL of tetrahydrofuran, lithium tetrahydroaluminate (17.7 mL, 1.00 M in tetrahydrofuran, 17.7 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 40% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (25, 1.79 g, 58%). MS (ESI) [M−H+]−=348.4.

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 40% ethyl acetate in hexane
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b642418054c142fda5efffcbdd3f7062
Source dataset
uspto-grants-2012_02
Patent number
US08110576B2

Reaction notes

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