Hydrochloric Acid → ethyl (2S)-2-[(1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-5-ylcarbonyl)amino]propanoate

HRID 916611Notes

Reaction equation

HRID 916611 reaction equation
[CH2:1]1[C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([C:13]([NH:15][C@@H:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:14])[C:6]=3[NH:5][C:4]=2[CH2:3][CH2:2]1.Cl>C(O)C.[Pd]>[CH2:1]1[CH:12]2[CH:4]([NH:5][C:6]3[C:7]([C:13]([NH:15][C@@H:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:14])=[CH:8][CH:9]=[CH:10][C:11]=32)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12132975ethyl (2S)-2-[(1,2,3,4-tetrahydrocyclopenta[b]indol-5-ylcarbonyl)amino]propanoate

Product 1

HCID 12132976ethyl (2S)-2-[(1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-5-ylcarbonyl)amino]propanoateYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of ethyl (2S)-2-[(1,2,3,4-tetrahydrocyclopenta[b]indol-5-ylcarbonyl)amino]propanoate (8.4 mmol, 2.5 g) in ethanol (40 mL) was added to a mixture of 5% palladium on carbon (2 g) in ethanol (20 mL). Concentrated hydrochloric acid (10 mL) was added and the resulting mixture was hydrogenated at 45 psi for 4 hours. The reaction mixture was filtered through Celite. The filter bed was washed well with ethanol and the combined filtrates were concentrated. The resulting oil was partitioned between 1 N NaOH and ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated to yield an oil (1.9 g, 6.1 mmol, 73% yield).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washThe filter bed was washed well with ethanol
  3. concentrationthe combined filtrates were concentrated
  4. customThe resulting oil was partitioned between 1 N NaOH and ethyl acetate
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ef3d3f163cff4a49b7ccb5fe6253893e
Source dataset
uspto-grants-2007_09
Patent number
US07271163B2

Reaction notes

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