Ethanol → HCID 54275090, compound

HRID 2298071Notes

Reaction equation

HRID 2298071 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([CH3:22])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].C(O)C>[Fe].O>[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([CH3:22])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 54373809HCID 54373809, compound

Product 1

HCID 54275090HCID 54275090, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

[1-(3-Methyl-4-nitrophenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (1.744 g, Example 35a), iron powder (1.52 g), ammonium chloride (1.45 g), ethanol (50 ml) and water (50 ml) were refluxed together under nitrogen for 2 h. The mixture was cooled and the iron was filtered off. Water (200 ml) was added to the residue and the product extracted into ethyl acetate (3×200 ml), dried (MgSO4), and concentrated to give the subtitle compound (1.56 g).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe iron was filtered off
  3. additionWater (200 ml) was added to the residue
  4. extractionthe product extracted into ethyl acetate (3×200 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ab01572e29804bbfaf8eb9259c9950a3
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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