Ethanol → HCID 25001714, compound

Temperature

0 °C

In a round bottom flask equipped with a magnetic stirring bar and a septum was placed (S,S) diethyl aziridine-2,3-dicarboxylate (1.87 g, 10 mmol) dissolved into 30 ml of EtOH. The vessel was cooled to 0° C. and NaBH4 (302.6 mg, 8 mmol) was added slowly. The reaction mixture was allowed to stir at 0° C. until the reaction was complete according to TLC (EtOAc, Rf=0.66), which was approximately 2 hours. The reaction was quenched by the addition of pH 7 phosphate buffer, and extracted three times with CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel; gradient 8:2 EtOAc/hexanes—100% EtOAc) to afford the title compound in 84% yield as a pale yellow oil. 1H NMR (CDCl3, 200 MHz) δ: 4.22 (q, J=7.0 Hz, 2H), 3.82 (dd, J=12.4 Hz, 2.8 Hz, 1H), 3.48 (dd, J=12 Hz, 4.8 Hz, 1H), 2.46 (m, 2H), 1.50 (bs, 1H), 1.31 (t, J=7.0 Hz, 3H) ppm. 13C NMR (CDCl3, 50 MHz) δ: 172.2, 62.0, 61.5, 39.8, 32.7, 14.3 ppm. HRMS (ESI) [M+H]+ calcd. for C6H12NO3 146.0817, found 146.0820.

1. customIn a round bottom flask equipped with a magnetic stirring bar
2. customThe reaction was quenched by the addition of pH 7 phosphate buffer
3. extractionextracted three times with CH2Cl2
4. dry with materialThe combined organic layers were dried over Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by flash column chromatography (silica gel; gradient 8:2 EtOAc/hexanes—100% EtOAc)

ORD record

ord-c8ac6fbfe2ea4a76a14f3744860f6936

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143375B2