Sodium Dithionite → (2S)-1-(2,3-Diaminophenoxy)-3-(dibenzylamino)propan-2-ol

HRID 2393943Notes

Reaction equation

HRID 2393943 reaction equation
[CH2:1]([N:8]([CH2:16][C@H:17]([OH:30])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[C:21]=1[NH2:29])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C.O>[CH2:1]([N:8]([CH2:16][C@H:17]([OH:30])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[C:21]=1[NH2:29])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 54232526(S)-[3-(N,N-Dibenzylamino)-2-hydroxypropoxy]-2-amino-3-nitrobenzene

Product 1

HCID 54261304(2S)-1-(2,3-Diaminophenoxy)-3-(dibenzylamino)propan-2-olYield 89.7%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

(S)-[3-(N,N-Dibenzylamino)-2-hydroxypropoxy]-2-amino-3-nitrobenzene (10.6 g, 26.0 mmol) was suspended in 1 L of 2:1 ethanol/water at ambient temperature and treated with excesses of sodium bicarbonate (26.22 g, 0.31 mol) and sodium hydrosulfite (54.34 g, 0.31 mol). The orange reaction mixture slowly became colorless over 1 hour, and the mixture was left to stir at ambient temperature for 16 hours. The suspension was filtered, and the filtrate concentrated in vacuo to a leave a white solid. This residue was partitioned between chloroform and water, and the organic layer washed twice with brine. The combined organic extracts were concentrated in vacuo to give 8.8 g of a brown oil. The compound was recrystallized rapidly from toluene to give 7.96 g (81%) of pale brown needles. NMR.

Workup

  1. waitthe mixture was left
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate concentrated in vacuo to
  4. customa leave a white solid
  5. customThis residue was partitioned between chloroform and water
  6. washthe organic layer washed twice with brine
  7. concentrationThe combined organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-9cc58210f38442d2a49c7175f6d8d098
Source dataset
uspto-grants-1998_09
Patent number
US05808080

Reaction notes

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