Ammonium formate → HCID 69415630, compound

HRID 853091Notes

Reaction equation

HRID 853091 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:34][C@@H:33]([CH3:35])[N:11]2[C:12]3[CH:13]=[C:14]([N:19]=C(C4C=CC=CC=4)C4C=CC=CC=4)[CH:15]=[CH:16][C:17]=3[CH2:18][C@@H:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].CO.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:34][C@@H:33]([CH3:35])[N:11]2[C:12]3[CH:13]=[C:14]([NH2:19])[CH:15]=[CH:16][C:17]=3[CH2:18][C@@H:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 86590242HCID 86590242, compound

Product 1

HCID 69415630HCID 69415630, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (4R,10aR)-7-(benzhydrylidene-amino)-4-methyl-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester (3.35 g, 7.2 mmol), ammonium formiate (6.8 g, 107 mmol) and palladium on carbon (1.5 g, 5%) in methanol (35 mL) was heated to 60° C. for 1 h. After cooling the mixture was diluted with dichloromethane (100 mL) and filtered. The filtrate was washed with water (100 mL), the water phase was extracted with dichloromethane, and organic phases were pooled and dried with MgSO4. The solvents were removed in vacuo and the residue was purified by chromatography on silica gel with ethylacetate/n-hexane (1:1). The title product was isolated as yellow foam (1.15 g, 53%); ISP-MS: m/e=304.4 (M+H+).

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationfiltered
  3. washThe filtrate was washed with water (100 mL)
  4. extractionthe water phase was extracted with dichloromethane, and organic phases
  5. dry with materialdried with MgSO4
  6. customThe solvents were removed in vacuo
  7. customthe residue was purified by chromatography on silica gel with ethylacetate/n-hexane (1:1)

Sources & evidence

ORD record
ord-9b8abec96fad46909913731c80174eb7
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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