Sodium Hydroxide → (R)-tert-Butyl (oxiran-2-ylmethyl)carbamate

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Reaction Conditions

Reaction Steps

((S)-2,3-Dihydroxypropyl)carbamic acid tert-butyl ester (5.00 g, 26.16 mmol) obtained in Step 1 above was dissolved in pyridine (32 ml), and cooled to 0° C. Methanesulfonyl chloride (2.22 ml, 28.71 mmol) was dropwise added to the solution, and stirred for 10 minutes. This solution was dropwise added to a solution of sodium hydroxide (3.18 g, 79.61 mmol) in water (33 ml) and dimethylsulfoxide (22 ml) at 0° C., and stirred for 10 minutes. This reaction solution was poured into ice water (300 ml), and then extracted with a mixture of n-hexane (80 ml) and ethyl acetate (320 ml). The organic layer was separated and washed with water and a saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. After the inorganic salt was removed by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane to n-hexane:ethyl acetate=4:1) to yield (R)-1-oxiranylmethylcarbamic acid tert-butyl ester (2.26 g).

Provenance & Evidence