Tert-butyl 2-(4-nitro-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate → Tert-butyl 2-(4-amino-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

HRID 2036737Notes

Reaction equation

HRID 2036737 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:21]=[C:20]([CH3:22])[C:19]3[N:18]([CH3:23])[C:17]4[CH2:24][CH:25]5[NH:29][CH:28]([C:16]=4[C:15]=3[C:14]=2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][CH2:26]5)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([S:10]([C:13]2[CH:21]=[C:20]([CH3:22])[C:19]3[N:18]([CH3:23])[C:17]4[CH2:24][CH:25]5[NH:29][CH:28]([C:16]=4[C:15]=3[C:14]=2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][CH2:26]5)(=[O:11])=[O:12])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 67085768Tert-butyl 2-(4-nitro-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67085597Tert-butyl 2-(4-amino-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateYield 75.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product of step A (43 mg, 0.08 mmol) in ethanol (5 mL) was added 5% palladium on carbon (60 mg). The reaction flask was purged with hydrogen and the reaction mixture was stirred at ambient temperature for 4 h before it was filtered through a celite bed. The filtrate was concentrated in vacuo to give tert-butyl 2-(4-amino-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (29 mg, 72%) as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.00 (s, 1H), 7.71 (dd, J=6.9, 1.8 Hz, 2H), 7.29 (s, 1H), 6.62 (dd, J=6.9, 1.8 Hz, 2H), 5.22 (br s, 1H), 4.69 (br s, 1H), 4.04 (s, 2H), 3.82 (s, 3H), 3.34 (br s, 1H), 2.72 (s, 3H), 2.44 (d, J=15.9 Hz, 1H), 2.08-2.37 (m, 2H), 1.86-1.97 (m, 1H), 1.52-1.65 (m, 1H), 1.37 (br s, 9H).

Workup

  1. customThe reaction flask was purged with hydrogen
  2. filtrationwas filtered through a celite bed
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1b07315ea923479db20b3dbadd0d11d5
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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