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

HRID 626394

反応式

HRID 626394 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-921f5ff9179f466080749db28a49f4e2
出典データセット
uspto-grants-2016_04
特許番号
US09309227B2

関連ノート

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