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 dichloromethane, CH2Cl2, (440 mL), D-(−)-diisopropyl tartrate (4 mL, 14.2 mmol) and 2-methyl-2-propene-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 dichloromethane and the mixture was stirred at −20° C. for 30 min. Cumene hydroperoxide (75 mL, 430 mmol) was added dropwise over 1.5 hours maintaining the temperature at −20° C. The mixture was stirred at this temperature overnight. Trimethyl phosphite (40 mL, 340 mmol) was added dropwise over 5 hours maintaining the temperature at −20° C. Triethyl amine (50 mL, 360 mmol) and 4-dimethylaminopyridine (DMAP) (3.48 g, 28.5 mmol) was added followed by a solution of 3-nitrobenzenesulphonyl chloride (47 g, 212 mmol) in dichloromethane (400 mL). The temperature was raised to −10° C. and the mixture was stirred at this temperature overnight. After removing the external cooling vessel, the reaction mixture was filtered through celite. The organic phase was washed with 10% tartaric acid (500 mL), saturated sodium hydrogencarbonate, NaHCO3, (300 mL) and brine (300 mL). The organic layer was dried over magnesium sulphate, MgSO4, and concentrated in vacuo to give 150 g of a yellow oil. The crude material was purified by silica gel flash chromatography (0-50% ethyl acetate in heptane) to give the subtitled compound (48.8 g).

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

ORD record

ord-a977ea3e4bfd4264852353ef52d45784

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07449475B2