Trifluoroacetic acid → HCID 67442226, compound

HRID 2045654Notes

Reaction equation

HRID 2045654 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([CH:25]=[CH:26][CH:27]=1)[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C:6]([CH3:29])([CH3:28])[CH:5]2O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([CH:25]=[CH:26][CH:27]=1)[C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[C:6]([CH3:29])([CH3:28])[CH2:5]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67441177HCID 67441177, compound

Product 1

HCID 67442226HCID 67442226, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a sealed tube was added benzyl 3-(6-chloro-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)benzoate (1.98 g, 4.70 mmol), dichloromethane (25 ml) and triethylsilane (1.10 g, 9.40 mmol, 2.0 eq.), followed by the addition of trifluoroacetic acid (1.61 g, 14.11 mmol, 3.0 eq.). The sealed tube was heated at 60 for 16 h and cooled to room temperature. The reaction mixture was washed with saturated Sodium bicarbonate and separated. The organic layer was dried the residue was purified by column chromatography using petroleum ether/ethyl acetate=20:1 to afford benzyl 3-(6-chloro-3,3-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)benzoate 914 mg (47.9% yield) as a yellow solid. MS (ESI+APCI) M+1=406.2.

Workup

  1. temperatureThe sealed tube was heated at 60 for 16 h
  2. washThe reaction mixture was washed with saturated Sodium bicarbonate
  3. customseparated
  4. customThe organic layer was dried the residue
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a436d8190b1c40d6a65d427819d34bb8
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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