Dimethyl Sulfide → 7-(4-(Trifluoromethoxy)phenyl)-3-thia-7,9-diazabicyclo[3.3.1]nonane

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Reaction Steps

A solution of 7-(4-(trifluoromethoxy)phenyl)-3-thia-7,9-diazabicyclo[3.3.1]nonane-6,8-dione (115 mg, 0.35 mmol) and THF (5 mL) was heated at 70° C. under N2. A solution of BH3.SMe2 (2M in THF, 0.7 mL, 1.4 mmol) was added dropwise. After 2.5 h, 6N HCl (1.0 mL) was added dropwise (Caution: H2 evolution). After an additional 30 min, the reaction was allowed to cool to rt, poured into 1N NaOH (8 mL), and extracted with dichloromethane (40 mL×2). The combined organic extracts were dried, filtered and concentrated to give 7-(4-(trifluoromethoxy)phenyl)-3-thia-7,9-diazabicyclo[3.3.1]nonane: MS (ESI): 305.5 (M+H).

Provenance & Evidence