Trifluoroacetic acid → HCID 23433566, compound

HRID 1938476Notes

Reaction equation

HRID 1938476 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[CH:11]([CH2:20][CH3:21])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:20]([CH:11]1[C:12]2[C:17](=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[NH:8][CH2:9][CH2:10]1)[CH3:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23433550HCID 23433550, compound

Product 1

HCID 23433566HCID 23433566, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a oven dried 250 mL r.b. flask equivuipped with a magnetic stir bar and a N2 gas inlet was dissolved (R/S)-1-t-butoxycarbonyl-4-ethyl-1,2,3,4-tetrahydro-7-methoxyquinoline (34.0 mg, 117 μmol) in dry CH2Cl2 (1 mL). To the stirred solution was added TFA (1.2 mL) at rt and was allowed to react for 2 h. The dark red solution was quenched with sat NaHCO3 solution (10 mL), extracted with CH2Cl2 (3×25 mL), washed with brine (50 mL), dried (Na2SO4) and concentrated in vacuo to afford 21 mg (95%) of the desired amine as a clear light yellow oil. Data for (R/S)-4-ethyl-1,2,3,4-tetrahydro-7-methoxyquinoline: Rf =0.1 (hexanes/EtOAc, 3: 1); 1H NMR (400 MHz, CDCl3) 6.92 (d, J=8.5, 1H), 6.21 (dd, J=2.5, 8.2, 1H), 6.03 (d, J=2.5, 1H), 3.73 (s, 3H), 3.27 (m, 2H), 2.59 (m, 1H), 1.86 (m, 1H), 1.75 (m, 2H), 1.48 (m, 1H), 0.968 (t, J=7.4, 3H).

Workup

  1. customIn a oven dried 250 mL r.b
  2. customflask equivuipped with a magnetic stir bar and a N2 gas inlet
  3. customto react for 2 h
  4. customThe dark red solution was quenched with sat NaHCO3 solution (10 mL)
  5. extractionextracted with CH2Cl2 (3×25 mL)
  6. washwashed with brine (50 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03847447310d4529880c0f236722d5a1
Source dataset
uspto-grants-1997_12
Patent number
US05693647

Reaction notes

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