Trifluoroacetic acid → HCID 68276484, compound

HRID 334429Notes

Reaction equation

HRID 334429 reaction equation
FC(F)(F)C(O)=O.[O:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.[NH2:33][C:34]1[CH:46]=[C:45]([CH:47]2[CH2:52][CH2:51][N:50]([CH3:53])[CH2:49][CH2:48]2)[CH:44]=[CH:43][C:35]=1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>ClCCl>[CH3:53][N:50]1[CH2:51][CH2:52][CH:47]([C:45]2[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:40])[CH3:41])=[O:37])=[C:34]([NH:33][CH:11]3[CH2:12][CH2:13][O:8][CH2:9][CH2:10]3)[CH:46]=2)[CH2:48][CH2:49]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 68276494HCID 68276494, compound

Product 1

HCID 68276484HCID 68276484, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.18 mL of 2,2,2-trifluoroacetic acid (93 mmol), 4.11 mg of dihydro-2H-pyran-4(3H)-one (44.5 mmol) and then 14.5 g of tetramethylammonium triacetoxyborohydride (53.8 mmol) are successively added to a solution of 15 g of tert-butyl 2-amino-4-(1-methylpiperidin-4-yl)benzoate in 200 mL of dichloromethane under stirring. The reaction medium is stirred at room temperature for 2 h and then taklen up with a 1N soda solution. The organic phase is isolated, dried on magnesium sulfate and then dried concentrated. The residue contained always HI. It is thus taken up in dichloromethane and washed with 100 mL of a 1H soda solution. The organic phase is decanted, dried on magnesium sulfate and dry concentrated to yield 14.6 g of a yellow solid (quantitative yield).

Workup

  1. stirringThe reaction medium is stirred at room temperature for 2 h
  2. customThe organic phase is isolated
  3. customdried on magnesium sulfate
  4. customdried
  5. concentrationconcentrated
  6. washwashed with 100 mL of a 1H soda solution
  7. customThe organic phase is decanted
  8. customdried on magnesium sulfate
  9. customdry
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-544fd7ca5e2e4b699f763dde51b053ce
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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