Water → (S)-N-((S)-1-(3-isopropylphenyl)ethyl)-2-methylpropane-2-sulfinamide

HRID 626396Notes

Reaction equation

HRID 626396 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6](/[C:10](=[N:12]/[S@:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])/[CH3:11])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].O.[BH4-].[Na+]>C1COCC1>[CH:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH:12][S@:13]([C:15]([CH3:18])([CH3:16])[CH3:17])=[O:14])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 90373684(NE,S)-2-methyl-N-[1-(3-propan-2-ylphenyl)ethylidene]propane-2-sulfinamide

Product 1

HCID 86732637(S)-N-((S)-1-(3-isopropylphenyl)ethyl)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S,E)-N-(1-(3-isopropylphenyl)ethylidene)-2-methylpropane-2-sulfinamide (9.5 g, 0.036 mol) in THF (98 mL)/H2O (2 mL) was added NaBH4, the mixture was stirred at room temperature for 16 hours. The mixture was then partitioned between EtOAc and water, the layers were separated and the organic layer was washed with water, brine, dried over Na2SO4, and concentrated. The residue was purified by column chromatography to give the titled compound.

Workup

  1. customThe mixture was then partitioned between EtOAc and water
  2. customthe layers were separated
  3. washthe organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-51299e1455e14536b14ddc16c9bd38c8
Source dataset
uspto-grants-2016_04
Patent number
US09309227B2

Reaction notes

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