Cyanamidnatrium → HCID 67053798, compound
Reaction equation
[N:1]#[C:2][NH2:3].[Na].[CH3:5][C:6]1([CH3:21])[CH2:15][CH2:14][CH2:13][C:12]2[CH:11]=[C:10]([O:16][CH2:17][C@@H:18]3[CH2:20][O:19]3)[CH:9]=[CH:8][C:7]1=2>CO>[CH3:21][C:6]1([CH3:5])[CH2:15][CH2:14][CH2:13][C:12]2[CH:11]=[C:10]([O:16][CH2:17][CH:18]3[O:19][C:2]([NH2:3])=[N:1][CH2:20]3)[CH:9]=[CH:8][C:7]1=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a vigorously stirred solution of sodium hydrogen cyanamide (0.52 g, 7.9 mmol) in methanol (20 mL) was added slowly (S)-2-(5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yloxymethyl)-oxirane (1.8 g, 7.9 mmol). The reaction mixture was stirred at room temperature overnight after which it was concentrated. Anhydrous diethyl ether (100 mL) was added. The resulting white precipitate was filtered and the filtrate concentrated. The residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride) to give 1.0 g (46%) of 5-(5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yloxymethyl)-4,5-dihydro-oxazol-2-ylamine.