Ammonia → 5-(tert-Butyl-dimethyl-silanyloxy)-cyclooctylamine

関与物質

反応手順

11.0 g (38.6 mmol) of titanium isopropoxide were added to a solution of 5.0 g (19.3 mmol) of 5-(tert-butyl-dimethyl-silanyloxy)-cyclooctanone (58) in 48.3 mL (96.5 mmol) of a 2M solution of ammonia in ethanol and stirred for 6 hours. After addition of 1.1 g (29 mmol) of sodium borohydride the mixture was stirred at room temperature for 4 days. The reaction was quenched by addition of 50 mL of a 2M aqueous ammonia solution. A white precipitate was removed by filtration and washed with ethyl acetate. The filtrate was extracted with ethyl acetate and the combined organic layers dried over magnesium sulfate, filtered and evaporated to yield 4.5 g of 5-(tert-butyl-dimethyl-silanyloxy)-cyclooctylamine (59) as a mixture of diastereomers as a yellow oil which was used without purification. Rt=2.14 min (Method J). Detected mass: 258.2 (M+H+).

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