trans-beta-METHYLSTYRENE → HCID 178455876, compound

HRID 962300Notes

Reaction equation

HRID 962300 reaction equation
C/C=C/c1ccccc1.CC(C)(C)C(=O)ON(Cc1ccccc1)Cc1ccccc1>C1CCOC1.CC(=O)[O-].CC(=O)[O-].CO[Si](C)OC.COc1c(C(C)(C)C)cc(P(c2cc(C(C)(C)C)c(OC)c(C(C)(C)C)c2)c2ccc3c(c2-c2c(P(c4cc(C(C)(C)C)c(OC)c(C(C)(C)C)c4)c4cc(C(C)(C)C)c(OC)c(C(C)(C)C)c4)ccc4c2OCO4)OCO3)cc1C(C)(C)C.[Cu+2].c1ccc(P(c2ccccc2)c2ccccc2)cc1>CC[C@H](c1ccccc1)N(Cc1ccccc1)Cc1ccccc1

Participants

8

Reactant 2

HCID 252325trans-beta-METHYLSTYRENEHCID 142744676(Dibenzylamino) 2,2-dimethylpropanoate

Product 1

HCID 178455876HCID 178455876, compoundYield 86%

Reagents, catalysts & solvents 5

HCID 6329250Dimethoxy(methyl)siliconReagentHCID 8895Cupric acetateCatalystHCID 11776TriphenylphosphineCatalystHCID 111941924,4'-Bi-1,3-benzodioxole-5,5'-diylbis{bis[4-methoxy-3,5-bis(2-methyl-2-propanyl)phenyl]phosphine}CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C
Other
After dropwise addition of dimethoxy(methyl)- silane into reaction mixture in water bath, the vessel was removed and allowed to stir for an additional 12 hours

Workup

  1. additionNo procedure recorded
  2. additionNo procedure recorded
  3. additionNo procedure recorded
  4. additionNo procedure recorded
  5. extraction3 x 50 mL ethyl acetate extraction · Keep organic
  6. concentrationrotary evaporator (35 degC, 50 mmHg)
  7. flash chromatographyThe crude reaction mixture is dissolved in a minimal quantity of benzene or toluene and is loaded onto a column, with interior diameter of roughly 2 inches, packed with silica (200 g, SiliCycle, F60/230-400 mesh) and equilibrated with hexanes. The column is eluted under air pressure with hexanes (500 mL), then 1% ethyl acetate in hexanes (1 L), then 2% ethyl acetate in hexanes (1 L). During elution, fractions are collected in test tubes (roughly 28 mL each), and the desired product typically elutes around fractions 18 through 66. The fractions that contain the productare combined
  8. concentrationrotary evaporator (30 degC, 80 mmHg)

Sources & evidence

ORD record
ord-7b927700e3414788865b46a4d4b18c44
Source dataset
Copper-Catalyzed Enantioselective Hydroamination of Alkenes
Original link
View source

Reaction notes

Loading…