(2-hydroxy-3-nitrophenyl)-((R)-3-hydroxypyrrolidin-1-yl)methanone → (3-amino-2-hydroxyphenyl)-((R)-3-hydroxypyrrolidin-1-yl)methanone

HRID 1528157Notes

Reaction equation

HRID 1528157 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[C:11]([N:13]1[CH2:17][CH2:16][C@@H:15]([OH:18])[CH2:14]1)=[O:12].[H][H]>CO.[Pd]>[NH2:8][C:7]1[C:2]([OH:1])=[C:3]([C:11]([N:13]2[CH2:17][CH2:16][C@@H:15]([OH:18])[CH2:14]2)=[O:12])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 89525381(2-hydroxy-3-nitrophenyl)-((R)-3-hydroxypyrrolidin-1-yl)methanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 58736084(3-amino-2-hydroxyphenyl)-((R)-3-hydroxypyrrolidin-1-yl)methanoneYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 7.83 g (26 mmol, 1 eq) of (2-hydroxy-3-nitrophenyl)-((R)-3-hydroxypyrrolidin-1-yl)methanone at 84% in 100 ml of methanol was stirred at hydrogen atmospheric pressure in the presence of 728 mg (10% by weight) of palladium on carbon at 10% for 16 hours. The reaction medium was filtered and the filtrate was evaporated. The residue was chromatographed on silica gel (column puriFlash IR-50SI/300G, Spot II) eluted with dichloromethane/methanol (96/4). 3.63 g of (3-amino-2-hydroxyphenyl)-((R)-3-hydroxypyrrolidin-1-yl)methanone were obtained in the form of a yellow amorphous solid. Yield=63%. SiO2/CH2Cl2 90: MeOH 10, developing with KMnO4.

Workup

  1. filtrationThe reaction medium was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel (column puriFlash IR-50SI/300G, Spot II)
  4. washeluted with dichloromethane/methanol (96/4)

Sources & evidence

ORD record
ord-a454bd71fc4d438c93afa147070e4f56
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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