1-Bromo-3-isopropylbenzene → (S)-1-(3-isopropylphenyl)ethanamine

HRID 626394

Reaction equation

HRID 626394 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([CH3:10])[CH3:9])[CH:3]=1.[Li]CCCC.CO[N:18](C)[C:19](=O)[CH3:20]>C1COCC1>[CH:8]([C:4]1[CH:3]=[C:2]([C@@H:19]([NH2:18])[CH3:20])[CH:7]=[CH:6][CH:5]=1)([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 1384991-Bromo-3-isopropylbenzeneHCID 537505N-Methoxy-N-methylacetamideHCID 178418339Butyllithium

Product 1

HCID 86674570(S)-1-(3-isopropylphenyl)ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-bromo-3-isopropylbenzene (10 g, 0.05 mol) in THF was added dropwise with BuLi (47 mL, 0.075 mol) at −60° C. After stirred 30 minutes, N-methoxy-N-methylacetamide (6.22 g, 0.06 mol) was added. The mixture was stirred at −30° C. for 3 hours. Then the mixture was quenched with H2O, the mixture was partitioned between EtOAc and water. The layer was separated and washed with water, brine, dried over Na2SO4, and concentrated. The residue was purified by column chromatography to obtained the titled compound.

Workup

  1. stirringThe mixture was stirred at −30° C. for 3 hours
  2. customThen the mixture was quenched with H2O
  3. customthe mixture was partitioned between EtOAc and water
  4. customThe layer was separated
  5. washwashed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-921f5ff9179f466080749db28a49f4e2
Source dataset
uspto-grants-2016_04
Patent number
US09309227B2

Linked notes

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