Triethylamine → HCID 67301244, compound

Temperature

-35 °C

Under a nitrogen atmosphere a mixture of 2.9 g (11.3 mmol) 3-(3-bromo-4-methyl-phenyl)-2-oxo-propionic acid and 2.0 mL (15.1 mmol) triethylamine in 40 mL THF was cooled to −35° C. Then a solution of 5.44 g (17.0 mmol) (1R)—B-chlorodiisopinocampheylborane in 20 mL THF was added dropwise so that the reaction temperature remained between −35° C. and −25° C.; the reaction mixture was kept for 1 h at this temperature, then the cooling bath was removed and the mixture was stirred overnight at RT. To complete the reaction another 3.0 g (9.4 mmol) (1R)—B-chlorodiisopinocampheylborane were added and the mixture was stirred for a further 5 h. While cooling with ice 30 mL 1 M NaOH and 30 mL TBME were added dropwise and the mixture was stirred for 15 min. The aqueous phase was separated off, the organic phase was extracted with 15 mL 1 M NaOH and 25 mL water. The combined aqueous phases were acidified with 2 M HCl while cooling with ice, extracted three times with 40 mL TBME and the combined organic phases were dried over Na2SO4. After the desiccant and solvent had been eliminated the residue was reacted further without purification.

1. customremained between −35° C. and −25° C.
2. customthe cooling bath was removed
3. additionwere added
4. stirringthe mixture was stirred for a further 5 h
5. additionwere added dropwise
6. stirringthe mixture was stirred for 15 min
7. customThe aqueous phase was separated off
8. extractionthe organic phase was extracted with 15 mL 1 M NaOH and 25 mL water
9. temperaturewhile cooling with ice
10. extractionextracted three times with 40 mL TBME
11. dry with materialthe combined organic phases were dried over Na2SO4
12. customwas reacted further without purification

ORD record

ord-42e121c386dc4e289a1e92d04e6b1e30

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700598B2