Ammonium formate → HCID 68356521, compound

HRID 2403309Notes

Reaction equation

HRID 2403309 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][C:16]=2[CH3:34])C2C=CC=CC=2)C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C>[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]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH2:22]2)=[CH:17][C:16]=1[CH3:34]

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 86671403HCID 86671403, compound

Product 1

HCID 68356521HCID 68356521, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of tert-butyl (RS)-2-(6-(diphenylmethyleneamino)-5-methylpyridin-3-yl)morpholine-4-carboxylate (1.0 g) in ethanol (100 ml) was added ammonium formate (14 g). The reaction mixture was degassed by bubbling argon into the mixture for several minutes. 10% Palladium on activated charcoal (2.56 mg) was then added and the reaction mixture was stirred at 80° C. for 2 hours. 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-amino-5-methylpyridin-3-yl)morpholine-4-carboxylate (246 mg, 38%) as a colourless oil. MS (ISP): 294.2 ([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 (2.56 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-f6b59c2e8e8d44f69538b698f0826ea8
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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