Triethylamine → HCID 11775986, compound

HRID 1969407Notes

Reaction equation

HRID 1969407 reaction equation
Br[CH2:2][C:3]([C:5]1([C:8]([O:10]CC)=O)[CH2:7][CH2:6]1)=[O:4].[CH3:13][C@@H:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN(CC)CC>C1COCC1>[CH3:13][C@@H:14]([N:21]1[CH2:2][C:3](=[O:4])[C:5]2([CH2:6][CH2:7]2)[C:8]1=[O:10])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6431891-Phenethylamine, (+)-HCID 11436266Ethyl 1-(2-bromoacetyl)cyclopropanecarboxylate

Product 1

HCID 11775986HCID 11775986, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-(2-bromoacetyl)cyclopropanecarboxylate (4.7 g, 20 mmol) in THF (60 mL) was added (R)-α-methylbenzylamine (2.9 g, 24 mmol) and Et3N (4.04 g, 40 mmol). After stirring at rt for 3 days, the reaction mixture was concentrated in vacuo, and the residue was extracted with ethyl acetate (50 mL×2) and washed with water (30 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc) to afford the title compound as a light yellow solid (3.66 g, 80%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. extractionthe residue was extracted with ethyl acetate (50 mL×2)
  3. washwashed with water (30 mL)
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (EtOAc)

Sources & evidence

ORD record
ord-969becad2bab4d43abf871e703367699
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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