Hydrochloric Acid → (R)-1-(4-Chloro-3,5-dimethyl-phenyl)-propylamine
Reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C@H:9]([NH:12][S@@](C(C)(C)C)=O)[CH2:10][CH3:11])=[CH:4][C:3]=1[CH3:19].Cl>CO>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C@H:9]([NH2:12])[CH2:10][CH3:11])=[CH:4][C:3]=1[CH3:19]Participants
4
Procedure
A solution of intermediate INT 37 (3.4 g, 11.26 mmol) in MeOH (75 mL) was treated with HCl (4 M in dioxane, 5.63 mL, 22.53 mmol) and stirred overnight. After evaporation of the solvents, a white solid was obtained which was washed with Et2O. The solid was then dissolved in water, slightly acidified with 2 M HCl and washed with EtOAc. The aqueous layer was separated and the pH adjusted to about 11 using 2 M NaOH followed by extraction with Et2O (3×). The Et2O layers were combined, dried over sodium sulfate, filtered and concentrated.