Iodine → 2-((1S,2S)-1-Ethyl-2-(phenylmethoxy)propyl)hydrazinecarboxaldehyde

Temperature

42.5 °C

A mixture of methyl tertiary butyl ether (150 ml), Mg turnings (18 g) and I2 (0.03 g) was heated to 40-45° C. under nitrogen atmosphere and ethyl bromide (81.8 g) was added slowly to the reaction mixture for about 1 hour. The reaction mixture was further heated to 50-55° C. and methyl tertiary butyl ether (60 ml) was added to it. The reaction mixture was stirred for 2 hours at 50-55° C. and cooled 0-10° C. N,O-Bistrimethyl silyl acetamide (60.9 g) was added to a mixture of methyl tertiary butyl ether (150 ml) and (S)—N′-(2-(benzyloxy)propylidene)formohydrazide compound of formula-16 (30 g) over a period of 45 minutes at 25-30° C. and stirred for 1 hour at 25-30° C. This reaction mixture was added to the above reaction mixture at 0-10° C. under nitrogen atmosphere. Temperature of the reaction mixture was raised to 25-30 C and stirred for 8 hours at 25-30° C. After completion of reaction, the reaction mixture was quenched with 8% acetic acid in chilled water. The reaction mixture was stirred for 30 minutes at 25-30° C. and both organic and aqueous layers were separated. The organic layer was washed with 10% sodium chloride solution and followed by water. Distilled off the solvent completely to get the title compound. The obtained compound was taken into next step without isolating the compound. Yield: 48 g

1. temperatureThe reaction mixture was further heated to 50-55° C.
2. temperaturecooled 0-10° C
3. stirringstirred for 1 hour at 25-30° C
4. additionThis reaction mixture was added to the above reaction mixture at 0-10° C. under nitrogen atmosphere
5. temperatureTemperature of the reaction mixture was raised to 25-30 C
6. stirringstirred for 8 hours at 25-30° C
7. customAfter completion of reaction
8. customthe reaction mixture was quenched with 8% acetic acid in chilled water
9. stirringThe reaction mixture was stirred for 30 minutes at 25-30° C.
10. customboth organic and aqueous layers were separated
11. washThe organic layer was washed with 10% sodium chloride solution
12. distillationDistilled off the solvent completely

ORD record

ord-eebf30ad9c17471089b6353d67ad7c70

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102664B2