2,3,3-Trimethylbut-1-ene → HCID 178461769, compound

HRID 962301Notes

Reaction equation

HRID 962301 reaction equation
C=C(C)C(C)(C)C.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>C[C@@H](CN(Cc1ccccc1)Cc1ccccc1)C(C)(C)C

Participants

8

Reactant 2

HCID 116692,3,3-Trimethylbut-1-eneHCID 142744676(Dibenzylamino) 2,2-dimethylpropanoate

Product 1

HCID 178461769HCID 178461769, compoundYield 87%

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
40 °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. temperatureNo procedure recorded
  2. additionNo procedure recorded
  3. additionNo procedure recorded
  4. additionNo procedure recorded
  5. additionNo procedure recorded
  6. extraction3 x 50 mL ethyl acetate extraction using a 250-mL separatory funnel · Keep organic
  7. concentrationrotary evaporator (35 degC, 50 mmHg)
  8. flash chromatographySilica (30 g) is added to the crude reaction mixture and the solvent removed in vacuo. This mixture 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 1% ethyl acetate in hexanes (2500 mL). During elution, fractions are collected in test tubes (roughly 28 mL each), and the desired product typically elutes around fractions 13 through 72 (Rf = 0.34). The fractions that contain the product are combined.
  9. concentrationrotary evaporator (30 degC, 80 mmHg)

Sources & evidence

ORD record
ord-e5c44ec1b5164f8ea077cf3b7ee0214a
Source dataset
Copper-Catalyzed Enantioselective Hydroamination of Alkenes
Original link
View source

Reaction notes

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