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Methyl 4-{[(tert-butoxycarbonyl)(methyl)amino]methyl}tetrahydro-2H-pyran-4-carboxylate

water

sodium hydroxide

→

title compound

수율 97.7%

4-{[(tert-butoxycarbonyl)(methyl)amino]methyl}tetrahydro-2H-pyran-4-carboxylic acid

수율 97.7%

용매

methanol

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후처리

1. 1
   온도The reaction was cooled to room temperature
2. 2
   기타volatiles were removed on a rotovap
3. 3
   workup.ADDITIONThe remaining solution was diluted with water
4. 4
   세척washed with ethyl acetate (2 times)
5. 5
   온도The water layer was cooled with an ice bath
6. 6
   workup.ADDITIONacidified with a mixture of 1 N aqueous HCl (28.1 mL) and saturated sodium chloride (28.1 mL)
7. 7
   추출The product was extracted with ethyl acetate (3 times)
8. 8
   건조the organic solution was dried over anhydrous sodium sulfate
9. 9
   여과filtered

실험 절차

Methyl 4-{[(tert-butoxycarbonyl)(methyl)amino]methyl}tetrahydro-2H-pyran-4-carboxylate (2.81 mmol) was dissolved in methanol (7.3 mL) and water (5.9 mL) and treated with 10 M sodium hydroxide (1.40 mL, 14.0 mmol). The solution was heated at 60° C. overnight. The reaction was cooled to room temperature, and volatiles were removed on a rotovap. The remaining solution was diluted with water and washed with ethyl acetate (2 times). The water layer was cooled with an ice bath and then acidified with a mixture of 1 N aqueous HCl (28.1 mL) and saturated sodium chloride (28.1 mL). The product was extracted with ethyl acetate (3 times), and the organic solution was dried over anhydrous sodium sulfate and filtered. Concentration of the organic solution gave the title compound (750 mg, 97% yield) which was used crude in the next step.

출처