Water → N-(5-((1R,2S)-2-(3,5-Bis(trifluoromethyl)benzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

HRID 1685897Notes

Reaction equation

HRID 1685897 reaction equation
[NH2:1][C@@H:2]([CH3:17])[C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].[F:18][C:19]([F:33])([F:32])[C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH:23]=O.O>CO>[F:18][C:19]([F:32])([F:33])[C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([C:28]([F:31])([F:29])[F:30])[CH:27]=1)[CH2:23][NH:1][C@@H:2]([CH3:17])[C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4]

Participants

5

Reactant 3

HCID 962WaterHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 58280635N-(5-((1R,2S)-2-Amino-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

Product 1

HCID 44628482N-(5-((1R,2S)-2-(3,5-Bis(trifluoromethyl)benzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamideYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the amine (4) (107 mg, 0.41 mmol) and 3,5-bis(trifluoromethyl)benzaldehyde (90 μL, 0.54 mmol) in methanol (4 mL) was added borane-pyridine complex (130 μL, 1.24 mmol) at 40° C. and the resulting mixture was stirred for 1.5 hours. The reaction mixture was cooled to room temperature and water was added thereto, followed by extraction with a mixed solvent (ethyl acetate:methanol=10:1) and subsequent washing of the organic layer with saturated brine. The organic layer was dried and concentrated and the obtained crude product was purified by amine silica gel column chromatography (eluent; chloroform:methanol=7:1) to obtain the desired amine (6) as a white solid (132 mg, Yield: 66%).

Workup

  1. extractionfollowed by extraction with a mixed solvent (ethyl acetate:methanol=10:1)
  2. washsubsequent washing of the organic layer with saturated brine
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customthe obtained crude product
  6. customwas purified by amine silica gel column chromatography (eluent; chloroform:methanol=7:1)

Sources & evidence

ORD record
ord-fa977ffeb8c64821bd3d3428ae52ed34
Source dataset
uspto-grants-2012_04
Patent number
US08148427B2

Reaction notes

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