Trifluoroacetic acid → HCID 9839506, compound

HRID 343919Notes

Reaction equation

HRID 343919 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:5][C@@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C@@H:7]1[N:15](C)[C:16](OC(C)(C)C)=O.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:5][C@@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C@@H:7]1[NH:15][CH3:16]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 53822127HCID 53822127, compound

Product 1

HCID 9839506HCID 9839506, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±) cis-1-(3,4-dichlorobenzyl)-2-(N-methyl-N-tert-butoxycarbonyl-amino)indane (1.016 g, 2.5 mmol) in dichloromethane (20 ml) at 0° C. was added trifluoroacetic acid (4 ml) dropwise. The solution was then stirred at room temperature for 2 h, poured into saturated aqueous NaHCO3 (150 ml) and extracted with dichloromethane (3×30 ml). The combined organic phases were dried over sodium sulfate, and concentrated in vacuo. The residue was subjected to column chromatography on silica eluting with 5% ethanol in chloroform to afford the title compound as a colourless oil (585 mg) which was converted to the HCl salt and crystallised to afford a white solid. m.p.>245° C. dec. (from ethanol-diethyl ether).

Workup

  1. extractionextracted with dichloromethane (3×30 ml)
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b61fe5ddae4c4453af44f5347cc24ca3
Source dataset
uspto-grants-1999_01
Patent number
US05863952

Reaction notes

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