Ammonium formate → HCID 23003959, compound

HRID 396718Notes

Reaction equation

HRID 396718 reaction equation
[C:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13](/[C:17](/[CH3:24])=[CH:18]\[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])=O.[NH4+]>C(O)C.[Pd]>[C:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]([CH3:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69563425HCID 69563425, compound

Product 1

HCID 23003959HCID 23003959, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 3-(1-boc-2,3-dihydro-1H-indol-5-yl)crotonate (11.4 g, Reference Example 7) and ammonium formate (about 30 g) in ethanol (about 200 ml) was warmed in an oil-bath to 60° C. Palladium on charcoal (10%, about 1 g) was added in one portion under a blanket of nitrogen—effervescence began almost immediately. The mixture was stirred at about 60° C. for about one hour, then cooled to room temperature and filtered through Celite. The filtrate was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was washed with water, then dried and then evaporated to give the title compound (11.1 g) as a colourless, mobile oil.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through Celite
  3. customThe filtrate was evaporated
  4. customthe residue was partitioned between water and ethyl acetate
  5. washThe organic layer was washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-857797184eb14f99a2f96a9637a15957
Source dataset
uspto-grants-2003_08
Patent number
US06608084B1

Reaction notes

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