Ethyl Acetate → HCID 11440041, compound

Participants

Reaction Steps

To a solution of (−)-(1S,3S)-4-[3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (910 mg, 2.21 mmol) (from Example 29d supra) in tetrahydrofuran (55 mL) at 0° C. was added in portions lithium aluminum hydride (250 mg, 6.63 mmol) (Aldrich). The reaction mixture was allowed to slowly warm up to room temperature. After stirring overnight the reaction mixture was poured in portions into a vigorously stirred mixture of ethyl acetate and saturated aqueous potassium sodium tartrate solution. The organic layer was collected, dried over sodium sulfate, filtered and concentrated to a solid that was then dissolved in dichloromethane (55 mL). To this solution was added manganese dioxide (1.92 g, 22.11 mmol) (Aldrich) and the mixture was stirred overnight. The slurry was filtered, the solids were washed with tetrahydrofuran (approximately 25 mL) and the combined organic layer was evaporated to a residue that was purified by chromatography on a silica gel column with a 0–50% diethyl ether in hexanes gradient to give (−)-(1S,3S)-4-[3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamino]-2-methylsulfanyl-pyrimidine-5-carbaldehyde as a viscous colorless oil. (Yield 615 mg, 76%).

Provenance & Evidence