Trifluoroacetic acid → HCID 66649710, compound

HRID 419379Notes

Reaction equation

HRID 419379 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][C@@H:22]4[CH2:24][C@H:19]3[CH2:20][N:21]4C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][C@@H:22]4[CH2:24][C@H:19]3[CH2:20][NH:21]4)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66649755HCID 66649755, compound

Product 1

HCID 66649710HCID 66649710, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1,1-dimethylethyl (1S,4S)-5-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1.0 g, 2.3 mmol) in DCM (10 mL) was added TFA (10 mL). After reaction was shown to be complete by TLC, the volume is reduced on the rotovap until it weighs 4 g. The solution is diluted with DCM and poured into saturated NaHCO3 solution. The layers are separated and the aqueous layer washed with DCM. The organics are combined, dried (MgSO4), filtered and rotovaped to give the title compound of step B (400 mg, 1.2 mmol, 50%). 1H NMR (400 MHz, CDCl3) δ 7.95 (d, J=9.3 Hz, 1H), 6.37 (dd, J=9.3, 2.6 Hz, 1H), 6.27 (d, J=2.6 Hz, 1H), 3.90 (s, 3H), 3.80-3.73 (m, 2H), 3.60 (br s, 2H), 3.20 (d, J=10.6 Hz, 1H), 3.12-2.95 (m, 4H), 2.87-2.81 (m, 1H), 2.64-2.55 (m, 1H), 2.36 (d, J=9.3 Hz, 1H), 1.94-1.77 (m, 3H), 1.64 (d, J=9.3 Hz, 1H), 1.59-1.46 (m, 2H). The aqueous layer is re-extracted with EtOAc and then with 85:15 DCM:iPrOH to give more of the title compound of step B (400 mg, 1.2 mmol, 50%).

Workup

  1. customAfter reaction
  2. customThe layers are separated
  3. washthe aqueous layer washed with DCM
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-030afa1168504a0ea8d506cb499159b6
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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