Potassium Carbonate → HCID 69423625, compound

Reaction equation

CC1(O)C(=[N:8][CH:9]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)CC2CC1C2(C)C.Cl.NO.C([O-])([O-])=O.[K+].[K+]>C(O)C>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C@H:9]([NH2:8])[CH2:10][CH2:11][CH:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH:19]=1

Participants

Procedure

To a solution of 2,6,6-trimethyl-3-(1-(3-pyridyl)-3-(4-oxanyl)propylimino]bicyclo[3.1.1]heptan-2-ol (1.85 g, 5.0 mmol) in ethanol (20 mL) was added hydroxylamine hydrochloride (2.00 g, 28.8 mmol) and K2CO3 (3.98 g, 28.8 mmol) and the mixture was heated to reflux for 16 h. The reaction was then cooled to room temperature, filtered through Celite, washed with ethanol, concentrated by rotary evaporation and purified by column chromatography, using a gradient of chloroform:methanol:ammonium hydroxide (90:9:1 to 80:19:1) eluent, to yield 0.88 g of a light yellow oil (80% yield).