Triethylamine → HCID 178498697, compound

HRID 628592

Reaction equation

HRID 628592 reaction equation
BrC(CBr)C(OC)=O.C(N(CC)CC)C.[C:16]1([C@@H:22]([N@:24]2[CH2:26][CH:25]2[C:27]([O:29][CH3:30])=[O:28])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[C:16]1([C@@H:22]([N@@:24]2[CH2:26][CH:25]2[C:27]([O:29][CH3:30])=[O:28])[CH3:23])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1.[C:16]1([C@@H:22]([N@:24]2[CH2:26][CH:25]2[C:27]([O:29][CH3:30])=[O:28])[CH3:23])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 95428Methyl 2,3-dibromopropionateHCID 178498697HCID 178498697, compound

Product 2

HCID 178498697HCID 178498697, compoundYield 37%HCID 178498698HCID 178498698, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To solution of methyl 2,3-dibromopropionate (25 mL, 198 mmol) in toluene at 5° C. was added triethylamine (55 mL, 0.39 mmol) in toluene (100 mL). After stirring for 5 min (S)-(1)-phenethylamine (25 mL, 198 mmol) in toluene (100 mL) was added dropwise. The suspension was refluxed for 3 h and allowed to cool down, filtered and the volatiles were evaporated under reduced pressure to give a residue that was purified by column chromatography (950 g of silica gel) with a gradient of 0-20% EtOAc in cyclohexane to yield to (S)-methyl 1-((S)-1-phenylethyl)aziridine-2-carboxylate EBE 06044A as a yellow oil (17.31 g, 43% yield) and (R)-methyl 1-((S)-1-phenylethyl)aziridine-2-carboxylate EBE 06044B as a yellow oil (15.14 g, 37% yield).

Workup

  1. additionwas added dropwise
  2. temperatureThe suspension was refluxed for 3 h
  3. temperatureto cool down
  4. filtrationfiltered
  5. customthe volatiles were evaporated under reduced pressure
  6. customto give a residue that
  7. customwas purified by column chromatography (950 g of silica gel) with a gradient of 0-20% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-91a06de6785f4afc89512fb2b6ecf7f9
Source dataset
uspto-grants-2016_04
Patent number
US09314466B2

Linked notes

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