Ammonium formate → HCID 68325614, compound

HRID 2403293Notes

Reaction equation

HRID 2403293 reaction equation
C1(C(=[N:14][C:15]2[N:20]=[CH:19][C:18]([CH:21]3[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]3)=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])=O.[NH4+]>CO>[NH2:14][C:15]1[N:20]=[CH:19][C:18]([CH:21]2[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 86671395HCID 86671395, compound

Product 1

HCID 68325614HCID 68325614, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of tert-butyl (RS)-2-(6-(diphenylmethyleneamino)pyridin-3-yl)morpholine-4-carboxylate (370 mg) in methanol (20 ml) was added ammonium formate (789 mg). The reaction mixture was degassed by bubbling argon into the mixture for several minutes. 10% Palladium on activated charcoal (44 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 the filtrate was concentrated in vacuo. The residue was taken up in EtOAc and the mixture was washed sequentially with water and with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: heptane/dichloromethane/MeOH) to afford tert-butyl (RS)-2-(6-aminopyridin-3-yl)morpholine-4-carboxylate (171 mg, 73%) as a light yellow oil. MS (ISP): 280.2 ([M+H]+).

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling argon into the mixture for several minutes
  3. addition10% Palladium on activated charcoal (44 mg) was then added
  4. filtrationThe reaction mixture was then filtered through celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. washthe mixture was washed sequentially with water and with saturated brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography (silica gel; gradient: heptane/dichloromethane/MeOH)

Sources & evidence

ORD record
ord-694f8a67ddcd4c529a1b3c8b0895cfac
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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