Lithium aluminum hydride → Propane-1 sulfonic acid (4 fluoro-3-hydroxymethyl-phenyl)-amide

HRID 250720Notes

Reaction equation

HRID 250720 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([NH:10][S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12])[CH:7]=[CH:6][C:5]=1[F:17].[AlH4-].[Li+]>O1CCCC1>[F:17][C:5]1[CH:6]=[CH:7][C:8]([NH:10][S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12])=[CH:9][C:4]=1[CH2:3][OH:2]

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 595068652-Fluoro-5-(propane-1-sulfonylamino)-benzoic acid methyl ester

Product 1

HCID 58087735Propane-1 sulfonic acid (4 fluoro-3-hydroxymethyl-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-Fluoro-5-(propane-1-sulfonylamino)-benzoic acid methyl ester (670, 1.20 g, 0.00436 mol) in tetrahydrofuran (100.0 mL) was added lithium tetrahydroaluminate (1.00 M in tetrahydrofuran, 10.0 mL) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight. To the reaction was added Na2SO4.10H2O (5 g), and then stirred at room temperature for 1 hour. The reaction was filtered, concentrated and purified with silica gel column chromatography eluting with 50% ethyl acetate in hexane to give the compound (671, 0.90 g, 83%). MS (ESI) [M−H+]−=246.1.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. custompurified with silica gel column chromatography
  5. washeluting with 50% ethyl acetate in hexane
  6. customto give the compound (671, 0.90 g, 83%)

Sources & evidence

ORD record
ord-bc8a2ec3408e4532ab725b012b253e84
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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