Benzyl Bromide → HCID 53877280, compound

Participants

Reaction Steps

A mixture of 500 mg (1.2 mmol) of t-butyl 4-(cyclohexylmethyl)-5-(4-hydroxy-2-isopropylbutyl)-2,2-dimethyl-3-oxazolidinecarboxylate in 3 ml of toluene, 191 mg (0.5 mmol) of tetrabutylammonium iodide, 5.9 g (150 mmol) of sodium hydroxide in water (8.8 ml) and 1.16 ml (9.8 mmol) of benzyl bromide is stirred at room temperature for 24 hours. Thereafter, water is added thereto, the mixture is extracted with ether, the ether extracts are dried over sodium sulphate and evaporated to dryness under reduced pressure. Chromatography of the residue on silica gel with a 1:8 mixture of ether and petroleum ether yields 457 mg (78.5%) of t-butyl (4S,5S)-5-[(S)-2-(benzyloxy)-2-isopropylbutyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate as a pale yellow resin, MS: 486 (M-CH3)+.

Provenance & Evidence