Trifluoroacetic acid → HCID 68385449, compound

HRID 534219Notes

Reaction equation

HRID 534219 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([C@@H:10]3[CH2:12][C@H:11]3[NH:13]C(=O)OC(C)(C)C)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>ClCCl>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([C@@H:10]3[CH2:12][C@H:11]3[NH2:13])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86708265tert-Butyl ((trans)-2-(4-cyclopropylphenyl)cyclopropyl)carbamate

Product 1

HCID 68385449HCID 68385449, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (trans-2-(4-cyclopropylphenyl)cyclopropyl)carbamate (260 mg, 0.951 mmol) in dichloromethane (DCM) (3 mL) was added TFA (500 μA, 6.49 mmol) and the mixture was stirred at room temperature for 3 h. The mixture was concentrated and the residue was treated with saturated NaHCO3 aqueous solution and extracted with DCM (3×). The extract was dried (Na2SO4) and concentrated to give 148 mg of product as pale yellow oil. MS: (M+H)+=174.1. 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.57-0.70 (m, 2H), 0.86-1.04 (m, 4H), 1.78-1.93 (m, 2H), 2.37-2.48 (m, 1H), 6.86-7.00 (m, 4H).

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-6916e5f07b5442c1be183f829c4f6e34
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

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