Trifluoroacetic acid → HCID 86708266, compound

HRID 529370Notes

Reaction equation

HRID 529370 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]([N:5]([CH2:15][C:16]1([C:29]([O:31][CH3:32])=[O:30])[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]1)[C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:4].C(O)(C(F)(F)F)=O>ClCCl>[F:34][C:2]([F:1])([F:33])[C:3]([N:5]([CH2:15][C:16]1([C:29]([O:31][CH3:32])=[O:30])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86708267HCID 86708267, compound

Product 1

HCID 86708266HCID 86708266, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butyl 4-methyl 4-((2,2,2-trifluoro-N-(trans-2-phenylcyclopropyl)acetamido)methyl)piperidine-1,4-dicarboxylate (150 mg, 0.310 mmol) in dichloromethane (DCM) (2 mL) was added TFA (0.5 mL, 6.49 mmol), and the mixture was stirred at room temperature for 2 h. The mixture was concentrated and the residue was treated with saturated NaHCO3 aqueous solution, extracted with DCM (3×). The extract was dried (Na2SO4) and concentrated to give 110 mg of product as oil. MS: (M+H)+=385.2. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.37-1.67 (m, 4H), 2.11-2.32 (m, 2H), 2.42 (ddd, J=10.17, 6.51, 3.54 Hz, 1H), 2.57 (m, J=12.60, 12.60, 5.87, 2.78 Hz, 2H), 2.90-3.07 (m, 2H), 3.17 (dt, J=7.45, 3.60 Hz, 1H), 3.52-3.58 (m, 3H), 3.70-3.84 (m, 2H), 7.10 (d, J=7.07 Hz, 2H), 7.19-7.26 (m, 1H), 7.28-7.35 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was treated with saturated NaHCO3 aqueous solution
  3. extractionextracted with DCM (3×)
  4. dry with materialThe extract was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-20e79a427d59475c8f11fa4c108ef980
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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