Trifluoroacetic acid → (R)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-methyl-propylamine

HRID 1182106Notes

Reaction equation

HRID 1182106 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH3:23])[CH2:9][CH2:10][N:11]1[CH2:14][CH:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:12]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH:13]2[CH2:14][N:11]([CH2:10][CH2:9][C@H:8]([NH2:7])[CH3:23])[CH2:12]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69410570{(R)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-methyl-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 69409912(R)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-methyl-propylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {(R)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-methyl-propyl}-carbamic acid tert-butyl ester (0.019 mg, 0.053 mmol) in DCM (1 ml) is treated with trifluoroacetic acid (0.042 ml) and stirred at room temperature overnight. The solvent is evaporated and the residue partition between DCM and 1M sodium hydroxide solution. The aqueous phase is extracted with more DCM (×3) and the combined organic phases washed with brine, dried over magnesium sulphate and evaporated to afford (R)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-methyl-propylamine. [M+H] 255.22

Workup

  1. customThe solvent is evaporated
  2. customthe residue partition between DCM and 1M sodium hydroxide solution
  3. extractionThe aqueous phase is extracted with more DCM (×3)
  4. washthe combined organic phases washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-c7a5cdc67f3249c5ac206621a3516d70
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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