Trifluoroacetic acid → (S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propylamine

HRID 1182104Notes

Reaction equation

HRID 1182104 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:23][O:24][CH3:25])[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>ClCCl>[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])[CH2:23][O:24][CH3:25])[CH2:12]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69411661{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 69410633(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propyl}-carbamic acid tert-butyl ester (0.87 g, 2.26 mmol) in dichloromethane (7 ml) is treated with trifluoroacetic acid (2 ml), and stirred at ambient temperature for 18 hours. The solvent is evaporated and the residue taken up in water, made alkali with 4.0 M aqueous sodium hydroxide solution and extracted into dichloromethane. The organic phase is dried over MgSO4 and evaporated to afford (S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propylamine. [MH]+ 285.20

Workup

  1. customThe solvent is evaporated
  2. extractionextracted into dichloromethane
  3. dry with materialThe organic phase is dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-9f1315286e424df7a3e435b0c0143809
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

Loading…