Trifluoroacetic acid → HCID 59371324, compound

HRID 2095395Notes

Reaction equation

HRID 2095395 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59371309HCID 59371309, compound

Product 1

HCID 59371324HCID 59371324, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3(R)-[3-(benzyloxy)propyl]pyrrolidine-1-carboxylate (170 mg, 0.53 mmol) in 2 mL of CH2Cl2 was added CF3COOH (0.5 mL) at room temperature under N2. The solution was stirred for 3 h at room temperature and then concentrated under vacuum. To the residue was added 20 mL of water, and the solution was washed with 30 mL of petroleum ether. The aqueous layer was adjusted to pH 8.0 with 2M aqueous NaHCO3 solution. The product was extracted into CH2Cl2 (3×40 mL), and the combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the free amine (115 mg, 99%) as a yellowish oil. LC-MS (ESI) m/z 220 (M+H+).

Workup

  1. concentrationconcentrated under vacuum
  2. additionTo the residue was added 20 mL of water
  3. washthe solution was washed with 30 mL of petroleum ether
  4. extractionThe product was extracted into CH2Cl2 (3×40 mL)
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e90047a4f9e84f86b4078dc829ebb4de
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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