Ammonium formate → (S)-Tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate

HRID 1520763Notes

Reaction equation

HRID 1520763 reaction equation
C1(C(=[N:14][C:15]2[CH:20]=[CH:19][C:18]([C@@H: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.[Pd]>[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H: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

5

Reactant 2

HCID 2723923Ammonium formateHCID 86654632(S)-tert-butyl 2-(4-(diphenylmethyleneamino)phenyl)morpholine-4-carboxylate

Product 1

HCID 66705988(S)-Tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylateYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of (S)-tert-butyl 2-(4-(diphenylmethyleneamino)phenyl)morpholine-4-carboxylate (54.1 g, 122 mmol), ammonium formate (116 g, 1.83 mol) and Pd/C 5% (6.5 g, 3.06 mmol) in methanol (930 ml) was stirred at 60° C. for 2 h. The reaction mixture was filtered and concentrated. The residue was dissolved in ethyl acetate and water. The organic phase was extracted twice with 0.5M HCl. The combined aqueous phases were basified with 2M-NaOH and extracted twice with DCM. The organic phases were dried over magnesium sulfate, filtered and dried in vacuo, to yield 31.95 g off-white solid. MS (ISP): 279.1 ([M+H]+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. extractionThe organic phase was extracted twice with 0.5M HCl
  5. extractionextracted twice with DCM
  6. dry with materialThe organic phases were dried over magnesium sulfate
  7. filtrationfiltered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-1fbe18ed13bf4d389a72d5ab2a4a8bad
Source dataset
uspto-grants-2015_07
Patent number
US09073911B2

Reaction notes

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