Trifluoroacetic acid → (S)-2-amino-4-[3-(4-chlorophenoxy)-azetidin-1-yl]-butan-1-ol

HRID 1182085Notes

Reaction equation

HRID 1182085 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:23][OH:24])[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>[NH2:7][C@@H:8]([CH2:9][CH2:10][N:11]1[CH2:14][CH:13]([O:15][C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)[CH2:12]1)[CH2:23][OH:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69410725{(S)-3-[3-(4-chlorophenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 11184815(S)-2-amino-4-[3-(4-chlorophenoxy)-azetidin-1-yl]-butan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {(S)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-carbamic acid tert-butyl ester. (0.46 g, 1.24 mmol) in dichloromethane (6 ml) is treated with trifluoroacetic acid (2 ml) and the reaction mixture stirred for 1 hour at ambient temperature. The solvent is evaporated and the residue dissolved in water. The resulting aqueous solution is basified with saturated aqueous NaHCO3 and extracted into dichloromethane. The dichloromethane is dried over MgSO4 and evaporated to afford (S)-2-amino-4-[3-(4-chlorophenoxy)-azetidin-1-yl]-butan-1-ol as a clear oil. [MH]+ 271.0

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue dissolved in water
  3. extractionextracted into dichloromethane
  4. dry with materialThe dichloromethane is dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-e7c6a7e7b72343bb8e3f1a263ba4e0a9
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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