Pivaloyl chloride → (Dibenzylamino) 2,2-dimethylpropanoate

HRID 962299Notes

Reaction equation

HRID 962299 reaction equation
CC(C)(C)C(=O)Cl.ON(Cc1ccccc1)Cc1ccccc1>CN(C)c1ccncc1.ClCCl>CC(C)(C)C(=O)ON(Cc1ccccc1)Cc1ccccc1

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 69297Dibenzylhydroxylamine

Product 1

HCID 142744676(Dibenzylamino) 2,2-dimethylpropanoateYield 93.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineReagentHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C
Other
reaction started in ice bath before addition of pivaloyl chloride, then allowed to warm to 23 C, then stirred for ' an additional 6 hours at RT (23 degC)

Workup

  1. additionNo procedure recorded
  2. additionNo procedure recorded
  3. additionNo procedure recorded
  4. additionNo procedure recorded
  5. extraction3 x 50 mL DCM extraction in 1 L separatory funnel · Keep organic
  6. washNo procedure recorded
  7. concentrationrotary evaporator (30 degC, 80 mmHg)
  8. dissolutionNo procedure recorded
  9. flash chromatographyAluminum oxide (neutral, powder, reagent-grade) was purchased from J.T. Baker. The crude reaction mixture is suspended in dichloromethane (50 mL) and is loaded onto a column, with interior diameter of roughly 2 inches, packed with alumina (100 g) and wetted with hexanes. dichloromethane is used as the eluent, and fractions are collected in Erlenmeyer flasks (50 mL each). The desired product typically elutes in fractions 2 through 25. The fractions that contain the desired product are combined
  10. concentrationrotary evaporator (30 degC, 80 mmHg)
  11. dry in vacuumNo procedure recorded

Sources & evidence

ORD record
ord-352807a1f4c14595afeef50c6c39ae38
Source dataset
Copper-Catalyzed Enantioselective Hydroamination of Alkenes
Original link
View source

Reaction notes

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