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

HRID 2227736Notes

Reaction equation

HRID 2227736 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 (2 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 orgainc phase was dried over MgSO4, filtered and concentrated to yield an oil (1.9 g, 6.1 mmol, 73%).

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 orgainc phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1ac6e74f331d41e3a9c9ccdbe8c0ff48
Source dataset
uspto-grants-2002_07
Patent number
US06414144B1

Reaction notes

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