Triethylamine → HCID 86597620, compound

Temperature

-20 °C

To an oven-dried 1000 ml three-necked flask was added powdered activated molecular sieves (8.0 g, 4 Å) and CH2Cl2 (440 ml, dried over molecular sieves). D-(−)-Diisopropyl tartrate (3.0 ml, 14.2 mmol) and 2-methyl-2-propan-1-ol (20 ml, 240 mmol) was added and the mixture was cooled to −20° C. Titanium tetraisopropoxide (3.5 ml, 11.9 mmol) was added with a few ml of CH2Cl2 and the mixture was stirred at −20° C. for 30 minutes. Cumene hydroperoxide (75 ml, approx. 430 mmol) was added dropwise over 1.5 hours maintaining the temperature at −20° C. The mixture was stirred at this temperature over night. Trimethylphosphite (40 ml, 340 mmol) was added dropwise over 5 hours maintaining the temperature at −20° C. Triethylamine (50 ml, 360 mmol) and DMAP (3.48 g, 28.5 mmol) was added followed by a solution of 3-nitrobenzenesulphonyl chloride (47 g, 212 mmol) in CH2Cl2 (400 ml). The temperature was raised to −10° C. and the mixture was stirred at this temperature over night. After removing the external cooling, the reaction mixture was filtered through celite®. The organic phase was washed with 10% tartaric acid (500 ml), saturated NaHCO3 (300 ml) and brine (300 ml). The organic phase was dried (MgSO4) and evaporated to give ca 150 g of a yellow oil. The crude material was chromatographed (1 kg silica, Heptane/EtOAc 100:0 to 50:50 gradually increased polarity) to give 48.8 g (84%) of the sub-title compound as a yellow oil. The compound was pure enough to use further without any additional purification.

1. additionTo an oven-dried 1000 ml three-necked flask was added
2. temperaturemaintaining the temperature at −20° C
3. stirringThe mixture was stirred at this temperature over night
4. temperaturemaintaining the temperature at −20° C
5. temperatureThe temperature was raised to −10° C.
6. stirringthe mixture was stirred at this temperature over night
7. customAfter removing the external cooling
8. filtrationthe reaction mixture was filtered through celite®
9. washThe organic phase was washed with 10% tartaric acid (500 ml), saturated NaHCO3 (300 ml) and brine (300 ml)
10. dry with materialThe organic phase was dried (MgSO4)
11. customevaporated

ORD record

ord-de7db21710fd46b5a3b9c6ffbaf0ee93

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06911458B2