Trifluoroacetic acid → HCID 58258845, compound

HRID 2036754Notes

Reaction equation

HRID 2036754 reaction equation
[C:1]1([S:7]([C:10]2[CH:18]=[CH:17][C:16]3[N:15]([CH2:19][CH2:20][O:21][Si](C(C)(C)C)(C)C)[C:14]4[CH2:29][CH:30]5[NH:34][CH:33]([C:13]=4[C:12]=3[C:11]=2C(OC(C)(C)C)=O)[CH2:32][CH2:31]5)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH2:19][CH2:20][OH:21])[C:14]2[CH2:29][CH:30]4[NH:34][CH:33]([C:13]3=2)[CH2:32][CH2:31]4)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67085779HCID 67085779, compound

Product 1

HCID 58258845HCID 58258845, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of step A (110 mg, 0.30 mmol) in dichloromethane at 0° C. was added trifluoroacetic acid (0.57 ml, 7.5 mmol) and the reaction was stirred overnight. The reaction mixture was made basic with saturated sodium bicarbonate solution and extracted with dichloromethane. The dichloromethane layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was crystallized from dichloromethane to give 2-phenylsulfonyl-5-(2-hydroxy)ethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole (100 mg, 87%) as a white crystalline solid: 1H NMR (CDCl3, 300 MHz), δ 8.27 (s, 1H), 7.93-7.96 (m, 2H), 7.71 (dd, J=9.0, 1.2 Hz, 1H), 7.52-7.62 (m, 4H), 5.29-5.31 (m, 1H), 4.53 (br s, 1H), 4.24 (t, J=5.1 Hz, 2H), 3.81 (t, J=5.1 Hz, 2H), 3.54 (dd, J=17.4, 4.5 Hz, 1H), 3.12 (d, J=20.7 Hz, 1H), 2.23-2.46 (m, 3H), 1.93-1.97 (m, 1H).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe dichloromethane layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was crystallized from dichloromethane

Sources & evidence

ORD record
ord-0d353096de144465bde07b7784bfa578
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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