Water → HCID 26192471, compound

HRID 2095435Notes

Reaction equation

HRID 2095435 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][O:10][CH2:11][C@@H:12]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][O:10][CH2:11][C@@H:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 59371626HCID 59371626, compound

Product 1

HCID 26192471HCID 26192471, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3(R)-[(3-phenylpropoxy)methyl]pyrrolidine-1-carboxylate (600 mg, 1.88 mmol) in CH2Cl2 (15 mL) was added a mixture of CF3COOH (4.62 g, 40.5 mmol, 21.6 equiv.) and water (0.3 mL) at 0° C. under N2. The solution was stirred overnight at room temperature. After concentration in vacuo, water was added, and the solution was washed with hexane. The water phase was basified with saturated aqueous NaHCO3 solution and extracted with EtOAc. The combined organic phases were dried and concentrated to obtain the product (220 mg, 53%) as a yellow oil. LC-MS (ESI) m/z 220 (M+H+).

Workup

  1. concentrationAfter concentration in vacuo, water
  2. additionwas added
  3. washthe solution was washed with hexane
  4. extractionextracted with EtOAc
  5. customThe combined organic phases were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7a66c2745ac341c687e0b17d4d44f895
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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