Ammonia → 4-Allyl-4-amino-adamantan-1-ol
Reaktionsgleichung
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=O)[CH2:3]1)[CH2:9]2.CO.[CH2:15](B1OC(C)(C)C(C)(C)O1)[CH:16]=[CH2:17].[NH3:27]>>[CH2:15]([C:5]1([NH2:27])[CH:6]2[CH2:11][C:2]3([OH:1])[CH2:9][CH:8]([CH2:10][CH:4]1[CH2:3]3)[CH2:7]2)[CH:16]=[CH2:17]Komponenten
5
Versuchsvorschrift
5-Hydroxy-2-adamantanone (3.0 g, 18.1 mmol) was dissolved in a solution of ammonia in methanol (7N, 26 mL, 180 mmol, 10 eq.) and stirred for 15 min at room temperature. Then, 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane (5.4 mL, 28.9 mmol, 1.6 eq.) was added dropwise. The reaction mixture was stirred for 16 h at room temperature before the volatiles were removed in vacuo. The residue was taken up in methanol twice and evaporated, then lyophilized from water to give 4-allyl-4-amino-adamantan-1-ol (3) as a mixture of diastereomers. Rt=1.05 min, 1.79 min (Method 2). Detected mass: 270.3 (M+H+).