Trifluoroacetic acid → HCID 16113255, compound

HRID 451201Notes

Reaction equation

HRID 451201 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH2:15][CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[NH:23][CH:22]([C:27]3[C:35]([Br:36])=[CH:34][C:30]4[O:31][CH2:32][O:33][C:29]=4[CH:28]=3)[CH:21]3[CH2:37][CH:38]=[CH:39][CH:20]3[C:19]=2[CH:18]=1)(C)(C)C>ClCCl>[Br:36][C:35]1[C:27]([CH:22]2[CH:21]3[CH2:37][CH:38]=[CH:39][CH:20]3[C:19]3[CH:18]=[C:17]([CH2:16][CH2:15][NH2:14])[CH:26]=[CH:25][C:24]=3[NH:23]2)=[CH:28][C:29]2[O:33][CH2:32][O:31][C:30]=2[CH:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24178081HCID 24178081, compound

Product 1

HCID 16113255HCID 16113255, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triflouroacetic acid (1.2 mL) was added dropwise to a solution of {2-[4-(6-bromo-benzo[1,3]dioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-8-yl]-ethyl}-carbamic acid tert-butyl ester (0.15 g, 0.3 mmol) in dichloromethane (1.5 mL), and stirred at rt for 1 h. The reaction mixture was diluted with dichloromethane (15 mL) and washed with cold saturated NaHCO3. Organic layer dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was purified by preparative silica gel chromatography using 20% MeOH/DCM and gave the product as a colorless solid (0.115 g, 95%).

Workup

  1. washwashed with cold saturated NaHCO3
  2. dry with materialOrganic layer dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by preparative silica gel chromatography

Sources & evidence

ORD record
ord-27fc8fa2ee1e4510b0bdc370c2c2beb1
Source dataset
uspto-grants-2013_07
Patent number
US08487100B2

Reaction notes

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