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

HRID 626394

반응식

HRID 626394 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-921f5ff9179f466080749db28a49f4e2
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309227B2

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