Trifluoroacetic acid → Methyl (R)-3-(methylamino)-2,3-dihydro-1H-indene-5-carboxylate

HRID 1193254Notes

Reaction equation

HRID 1193254 reaction equation
C(O)(C(F)(F)F)=O.C(O[C:13]([N:15](C)[C@H:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[CH:23]=2)[CH2:18][CH2:17]1)=O)(C)(C)C>C(Cl)Cl>[CH3:13][NH:15][C@H:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[CH:23]=2)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59505713Methyl (R)-3-((tert-butoxycarbonyl)(methyl)amino)-2,3-dihydro-1H-indene-5-carboxylate

Product 1

HCID 59505421Methyl (R)-3-(methylamino)-2,3-dihydro-1H-indene-5-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (25 ml) was added dropwise at 0° C. to a solution of (R)-methyl 3-(tert-butoxycarbonyl-(methyl)amino)-2,3-dihydro-1H-indene-5-carboxylate (11.0 g, 36.60 mmol, 1.0 eq.) in DCM (100 ml) and stirring was carried out for 1 hour at RT. After monitoring by TLC, the reaction solution was concentrated under reduced pressure and the residue was taken up in sat. sodium hydrogen carbonate solution and extracted with ethyl acetate (3×1000 ml). The combined org. phases were dried over sodium sulfate, concentrated and used in the next stage without being purified further. Yield: 92% (6.8 g, 33.17 mmol).

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate (3×1000 ml)
  3. dry with materialphases were dried over sodium sulfate
  4. concentrationconcentrated
  5. customwithout being purified further

Sources & evidence

ORD record
ord-72861c73069b48b79acc5750a2ce115e
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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