Ammonium formate → HCID 68325506, compound

HRID 2403285Notes

Reaction equation

HRID 2403285 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]2[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C([O-])=O.[NH4+]>CO>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH:11]2[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:12]2)=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 68356519HCID 68356519, compound

Product 1

HCID 68325506HCID 68325506, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of tert-butyl (RS)-2-(3-methyl-4-nitrophenyl)morpholine-4-carboxylate (2.21 g) in methanol (100 ml) was added ammonium formate (6.48 g). The reaction mixture was degassed by bubbling argon into the mixture for several minutes. 10% Palladium on activated charcoal (219 mg) was then added and the reaction mixture was stirred at 60° C. for 1 hour. The reaction mixture was then filtered through celite and concentrated in vacuo. The residue was taken up in EtOAc and extracted sequentially with water and with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford tert-butyl (RS)-2-(4-amino-3-methylphenyl)morpholine-4-carboxylate (1.99 g, 99%) as a colourless oil. MS (EI): 292 (M+), 235 ([M-C4H9]+), 219 ([M-C4H9O]+), 191, 136, 57 ([C4H9]+).

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling argon into the mixture for several minutes
  3. addition10% Palladium on activated charcoal (219 mg) was then added
  4. filtrationThe reaction mixture was then filtered through celite and
  5. concentrationconcentrated in vacuo
  6. extractionextracted sequentially with water and with saturated brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a15edb87416a45d7b86dd59fa0ed9cd0
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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