Trifluoroacetic acid → HCID 86708247, compound

HRID 529350Notes

Reaction equation

HRID 529350 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([N:5]([CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]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:31][C:2]([F:1])([F:30])[C:3]([N:5]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86708246HCID 86708246, compound

Product 1

HCID 86708247HCID 86708247, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-(2,2,2-trifluoro-N-(trans-2-phenylcyclopropyl)acetamido)ethyl)piperidine-1-carboxylate (650 mg, 1.476 mmol) in dichloromethane (DCM) (4 mL) was added TFA (1 mL, 12.98 mmol), and the mixture was stirred at room temperature for 1.5 h. The mixture was concentrated and the residue was dissolved in DCM (20 mL). The resulting solution was washed with 10% NaHCO3 aqueous solution. The organic phase was collected and dried (Na2SO4) and concentrated. The residue was dried under vacuum to give 470 mg of product as oil. MS: (M+H)+=341.4. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.33-1.79 (m, 7H), 1.93-2.10 (m, 2H), 2.27-2.59 (m, 1H), 2.84-3.06 (m, 2H), 3.15-3.25 (m, 1H), 3.66 (t, J=7.20 Hz, 2H), 7.09-7.41 (m, 5H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in DCM (20 mL)
  3. washThe resulting solution was washed with 10% NaHCO3 aqueous solution
  4. customThe organic phase was collected
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-621c6178c78a42c49ad9f098a52e4ddd
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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