Sodium Hydroxide → HCID 178451370, compound

Reaction equation

[C:1]([O:5][C:6]([CH2:8][O:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([N:16]2CN(C)C(=O)N(C)C2)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].[OH-].[Na+]>C(O)(C)(C)C>[NH2:16][C@H:13]1[CH2:14][CH2:15][C@H:10]([O:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:11][CH2:12]1

Participants

Procedure

1H-NMR (CDCl3) δTMS : 4.20(s,4H), 3.98(s,2H), 3.49-3.23(m,1H), 2.84(s,6H), 2.88-2.75(m,1H), 2.18-2.06(m,2H), 2.06-1.93(m,2H), 1.47(s,9H), 1.44-1.16 (m,4H) trans-5-[4-[(t-Butoxycarbonyl)methyloxy]cyclohexyl]-1,3-dimethylhexahydro-2-oxo-1,3,5-triazine (300 mg, 0. 879 mmol) was dissolved in t-butanol (5 ml) and a saturated aqueous ammonium chloride solution (5 ml) was added, which was followed by refluxing under heating for 2 hours. The reaction mixture was adjusted to pH 10 with a 1N aqueous sodium hydroxide solution and extracted with benzene. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure and the residue was purified by silica gel column chromatography (methylene chloride/methanol=10/1-5/1) to give 130 mg of t-butyl trans-(4-aminocyclohexyloxy)acetate as a colorless solid (57%).