Potassium Bicarbonate → (3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)azetidin-2-one

Temperature

0 °C

The aldehyde (318 mg) obtained above was dissolved in methanol (5 ml) and the solution was cooled to 0° C. 1N Aqueous potassium hydrogen carbonate (0.5 ml) was added and the mixture was stirred at 0° C. for 5 minutes and at ambient temperature for 30 minutes. Sodium borohydride (38 mg) was then added to the mixture at 0° C. and the mixture was stirred at the same temperature for 15 minutes and quenched by addition of acetic acid (0.15 ml). After concentration in vacuo, the residue was dissolved in chloroform and washed with brine containing sodium hydrogen carbonate. The aqueous layer was extracted three times with chloroform. The combined extracts were dried over magnesium sulfate and evaporated in vacuo to give a crystalline solid, which was chromatographed on silica gel (6 g, eluting with 3-10% methanol in dichloromethane) to give 113 mg of (3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)azetidin-2-one.

1. stirringthe mixture was stirred at the same temperature for 15 minutes
2. customquenched by addition of acetic acid (0.15 ml)
3. concentrationAfter concentration in vacuo
4. dissolutionthe residue was dissolved in chloroform
5. washwashed with brine
6. additioncontaining sodium hydrogen carbonate
7. extractionThe aqueous layer was extracted three times with chloroform
8. dry with materialThe combined extracts were dried over magnesium sulfate
9. customevaporated in vacuo
10. customto give a crystalline solid, which
11. customwas chromatographed on silica gel (6 g, eluting with 3-10% methanol in dichloromethane)

ORD record

ord-1226eca71a9f4a83b0db23c4deb8b1d2

Source dataset

uspto-grants-1985_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04539152