Trifluoroacetic acid → HCID 59371502, compound

HRID 2095401Notes

Reaction equation

HRID 2095401 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 59371394HCID 59371394, compound

Product 1

HCID 59371502HCID 59371502, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3(S)-[3-(benzyloxy)propyl]pyrrolidine-1-carboxylate (495 mg, 1.55 mmol) in 6 mL of CH2Cl2 was added CF3COOH (1.5 mL) at room temperature under N2. The resulting 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 water layer was adjusted to pH 8.0 with 2 M aqueous NaHCO3 solution and extracted with CH2Cl2 (3×40 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo to give 3(S)-[3-(benzyloxy)propyl]pyrrolidine (330 mg, 97%) 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. extractionextracted with CH2Cl2 (3×40 mL)
  5. dry with materialThe organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2ae5ba333c54aeba7ad7c9529a79e6e
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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