Water → HCID 118194606, compound

Temperature

0 °C

With HBF4OEt2: (S,E)-N-butylidene-1-phenylethanamine (Example 1, 10.0 g, 57.0 mmol) was dissolved in 250 mL 2-methyltetrahydrofuran and cooled to 0° C. HBF4OEt2 (9.24 g, 57.0 mmol) was added to the mixture followed by a solution of trimethyl((1,2,2-triethoxyvinyl)oxy)silane (Example 10, 11.34 g, 45.6 mmol) in 80 mL 2-methyltetrahydrofuran, and the mixture was stirred at 0° C. for three hours and fifteen minutes. Water (400 mL) was added to quench the reaction, the mixture was neutralized (pH=7.6) with 10N NaOH, the phases were separated and the organic phase was extracted once more with further 400 mL water. Water (300 mL) and 2-methyltetrahydrofuran (50 mL) were added to the mixture, the pH was acidified (pH=5.6) with 2N HCl and the phases were separated. The organic phase was extracted with further 300 mL water and 50 mL 2-methyltetrahydrofuran and the solvent of the organic phase was removed in vacuo to yield 17.1 g crude (S)-ethyl 2,2-diethoxy-3-(((S)-1-phenylethyl)amino)hexanoate as a 86.14 (syn:anti) diastereomeric mixture.

1. additionHBF4OEt2 (9.24 g, 57.0 mmol) was added to the mixture
2. customto quench
3. customthe reaction
4. customthe phases were separated
5. extractionthe organic phase was extracted once more with further 400 mL water
6. additionWater (300 mL) and 2-methyltetrahydrofuran (50 mL) were added to the mixture
7. customthe phases were separated
8. extractionThe organic phase was extracted with further 300 mL water and 50 mL 2-methyltetrahydrofuran
9. customthe solvent of the organic phase was removed in vacuo

ORD record

ord-cd67cb2734f7430987361ebb786f30bf

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346853B2