Nitrogen → HCID 67128531, compound

Temperature

0 °C

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a degassed solution of dicyclohexylamine (1.03 mL, 5.18 mmol) in toluene (30 mL) was treated 0° C. with n-BuLi (2.07 mL of a 2.5M solution in hexane, 5.18 mmol) and the reaction was stirred at 0° C. for 30 min. Acetic acid tert-butyl ester (0.59 mL, 4.40 mmol) was added dropwise and the reaction mixture was stirred at 0° C. for 50 min. To this solution was added a degassed suspension of 2-(3-bromo-phenyl)-2-methyl-[1,3]dioxolane (972 mg, 4.00 mmol) and {[P(t-Bu)3]PdBr}2 (25 mg, 0.03 mmol) and the reaction mixture was stirred at rt for 5 h. The reaction volume was reduced to half by rotary evaporation. The concentrated solution was washed with sat. aq. NH4Cl (30 mL). A large amount of precipitate formed between the aq. and org. layers. The org. layer was separated, and the aq. layer was washed with ether (5×20 mL). The combined org. layers were dried over MgSO4, filtered, and the solvent was removed under reduced. Purification of the residue by FC (9:1 hept-EA) gave the title compound as a yellow oil. TLC: rf (9:1 hept-EA)=0.26. LC-MS-conditions 02: tR=1.05 min.

1. stirringthe reaction mixture was stirred at 0° C. for 50 min
2. additionTo this solution was added
3. stirringthe reaction mixture was stirred at rt for 5 h
4. customThe reaction volume was reduced to half by rotary evaporation
5. washThe concentrated solution was washed with sat. aq. NH4Cl (30 mL)
6. customA large amount of precipitate formed between the aq. and org
7. customlayer was separated
8. washthe aq. layer was washed with ether (5×20 mL)
9. dry with materiallayers were dried over MgSO4
10. filtrationfiltered
11. customthe solvent was removed
12. customPurification of the residue by FC (9:1 hept-EA)

ORD record

ord-87e4f8628df3471c8fe7d66b872d2cfb

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674111B2