Ammonia → 1-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctylamine

Beteiligte Stoffe

Reaktionsschritte

To a solution of 1.5 g (5.85 mmol) of 5-(tert-butyldimethylsilyloxy)cyclooctanone in 8.4 mL (58.5 mmol) of 7N ammonia in methanol, previously stirred for 15 min at room temperature, were added dropwise 1.7 mL (9.36 mmol) of 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane. The reaction mixture was stirred for 18 h at room temperature. The volatiles were removed in vacuo and the residue redissolved in 100 mL of diethyl ether. Then, 100 mL of 1 N aqueous HCl were added dropwise and the resultant biphasic mixture was stirred for 30 min. The layers were separated, the aqueous layer was washed with diethyl ether and the pH adjusted to pH9 by the addition of sodium hydroxide. The suspension was then extracted with a 3:1 mixture of dichloromethane and 2-propanol and the combined organic extracts were concentrated in vacuo to afford 0.89 g of the title compound as mixture of diastereomers. Rt=0.44 min, 0.49 min (Method C). Detected mass: 184.3 (M+H+).

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