Diisopropylamine → HCID 86757662, compound

Temperature

0 °C

To a solution of diisopropylamine (2.28 g, 20.63 mmol) in THF (20 mL) cooled to 0° C. is added n-butyllithium (20.63 mmol, 2.5 M in hexanes) and the resulting solution is stirred at 0° C. or 0.5 h. The reaction mixture is cooled to −50° C. followed by slow addition of ethyl (3R)-3-hydroxyhexanoate (1.5 g, 9.38 mmol). After 0.5 h a solution of cinnamyl bromide (2.67 g, 14.06 mmol) in HMPA (2 mL) is added and the reaction mixture is allowed to warm to −20° C. and stirred for 16 h. The reaction mixture is quenched by addition 3 mL of saturated aqueous ammonium chloride solution, is poured into 20 mL of 1 N hydrochloric acid, and is extracted with two 50-mL portions of EtOAc. The combined organic layers are dried over magnesium sulfate, concentrated in vacuo, and purified by silica gel chromatography (elution with 25% EtOAc-hexanes) to afford ethyl (2R,3R)-2-[(2E)-3-phenyl-2-propen-1-yl]-3-hydroxyhexanoate as a yellow oil (1.82 g, 70% yield).

1. temperatureThe reaction mixture is cooled to −50° C.
2. temperatureto warm to −20° C.
3. stirringstirred for 16 h
4. customThe reaction mixture is quenched by addition 3 mL of saturated aqueous ammonium chloride solution
5. additionis poured into 20 mL of 1 N hydrochloric acid
6. extractionis extracted with two 50-mL portions of EtOAc
7. dry with materialThe combined organic layers are dried over magnesium sulfate
8. concentrationconcentrated in vacuo
9. custompurified by silica gel chromatography (elution with 25% EtOAc-hexanes)

ORD record

ord-a0f91bf2e15d41608a8e2398a668a4ba

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06329400B1