Sodium Thiosulfate → 3-(N-ethylanilino)propane-1,2-diol

HRID 252022Notes

Reaction equation

HRID 252022 reaction equation
[CH2:1]([N:4](CC)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:2]=C.C[N+]1([O-])CC[O:17]CC1.[CH3:21][C:22]([CH3:24])=[O:23].O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C([O-])(O)=O.[Na+].O=[Os](=O)(=O)=O>[CH2:1]([N:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:21][CH:22]([OH:23])[CH2:24][OH:17])[CH3:2]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 13264654HCID 13264654, compoundHCID 18366337Propan-2-one--water (1/1)

Product 1

HCID 4586933-(N-ethylanilino)propane-1,2-diolYield 86%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of OsO4 (7.8 mL, 0.1 M in water, 0.03 eq.) was added to a mixture of allyl-ethyl-phenyl-amine (4.10 g, 25.3 mmol) and NMO (5.92 g, 2.0 eq.) in 9:1 acetone-water (40 mL) at room temperature and the resulting mixture was stirred overnight. The mixture was diluted with sat. NaHCO3 (80 mL), sat Na2S2O3 (20 mL) and 1:1 Et2O-hexanes (100 mL). The separated aqueous phase was extracted with 2×30 mL of EtOAc and the combined organic phase was dried over Na2SO4, filtered and concentrated and the product was purified by chromatography (30% EtOAc-hexanes) to give 3-(ethyl-phenyl-amino)-propane-1,2-diol (4.25 g, 86%).

Workup

  1. extractionThe separated aqueous phase was extracted with 2×30 mL of EtOAc
  2. dry with materialthe combined organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe product was purified by chromatography (30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-a58780a69d0244d68e0e932b13244154
Source dataset
uspto-grants-2011_01
Patent number
US07868002B2

Reaction notes

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