Trifluoroacetic acid → (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indole

HRID 602807Notes

Reaction equation

HRID 602807 reaction equation
C(OC([N:8]1[C:16]2[CH:15]=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=2[C:10]2[CH2:18][CH:19]([C:21]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])([CH3:25])[CH2:22][O:23][CH3:24])[CH2:20][C:9]1=2)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:29]1([S:26]([C:21]([CH:19]2[CH2:20][C:9]3[NH:8][C:16]4[CH:15]=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=4[C:10]=3[CH2:18]2)([CH3:25])[CH2:22][O:23][CH3:24])(=[O:27])=[O:28])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67267337(RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl ester

Product 1

HCID 46898365(RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indoleYield 27.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

52 mg (0.1 mmol) (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl ester were dissolved in 4 mL CH2Cl2 at 0° C. Then, 1 mL of TFA was added dropwise and the temperature was slowly raised to RT and the reaction was stirred for 20 minutes. The reaction was quenched with a saturated NaHCO3 solution. The organic phase was dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel (EtOAc/heptane 1:2) yielded 11 mg (26%) (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indole as a white powder, MS: 404 (MH|).

Workup

  1. customThe reaction was quenched with a saturated NaHCO3 solution
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-b45fb1d2c0804aac8d04bbc8fb3dd11c
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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