Phthalimide → HCID 54458704, compound

Participants

Reaction Steps

5.0 g (12.15 mmol) of t-butyl 4-(cyclohexylmethyl)-5-(4-hydroxy-2-isopropylbutyl)-2,2-dimethyl-3-oxazolidinecarboxylate, 4.68 g (17.8 mmol) of triphenylphosphine and 2.48 g (17 mmol) of phthalimide are dissolved in 70 ml of tetrahydrofuran and cooled to 10°. Then, a solution of 2.8 ml (17.8 mmol) of diethyl azodicarboxylate in 15 ml of tetrahydrofuran is added dropwise within 10 minutes and the reaction mixture is stirred at room temperature for 4 hours. Then, the reaction mixture is evaporated under reduced pressure and the residue is chromatographed on 160 g of silica gel with a mixture of methylene chloride and hexane as the eluting agent, whereby there are obtained 5.4 g of t-butyl (4S,5S)-4-(cyclohexylmethyl)-5-[(S)-2-isopropyl-4-phthalimidobutyl]-2,2-dimethyl-3-oxazolidinecarboxylate as an oil, MS: 525 (M-CH3)+.

Provenance & Evidence