Ammonium formate → HCID 67240315, compound

HRID 1520766Notes

Reaction equation

HRID 1520766 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 86654631HCID 86654631, compound

Product 1

HCID 67240315HCID 67240315, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of (R)-tert-butyl 2-(4-(diphenylmethyleneamino)phenyl)morpholine-4-carboxylate (6 g, 13.6 mmol), ammonium formate (12.8 g, 203 mmol) and Pd/C5% (721 mg, 0.339 mmol) in methanol (103 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 3.04 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-35d316cadbc74d4499e236aa56a5c87b
Source dataset
uspto-grants-2015_07
Patent number
US09073911B2

Reaction notes

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