Water → HCID 22935713、化合物

HRID 1352494ノート

反応式

HRID 1352494 の反応式
[CH3:1][CH:2]1[CH2:11][C:10](=[N:12][CH2:13][C:14]#[CH:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17].O>C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>[CH3:1][CH:2]1[CH2:11][CH:10]([NH:12][CH2:13][C:14]#[CH:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17]

参加物

5

反応物 2

HCID 962WaterHCID 22935746HCID 22935746、化合物

生成物 1

HCID 22935713HCID 22935713、化合物収率 17.6%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 5049666Sodium triacetoxyborohydride溶媒

実験手順

To a solution of (2-methyl-4-prop-2-ynylimino-3,4-dihydro-2H-quinolin-1-yl)-phenyl-methanone (0.5 g) in acetic acid (20 ml), sodium triacetoxyborohydride was added in small amounts (1.75 g) under stirring at room temperature. The reaction mixture was then stirred at room temperature for one hour and poured on 100 ml of cold water under stirring. The desired compound was filtered after precipitation. The compound was dissolved in ethyl acetate and washed with water. The organic layer was separated and dried over sodium sulfate. The solvent was removed under reduce pressure to give a brown oil which was purified by flash chromatography with cyclohexane/ethyl acetate (95/5) as eluent and then cyclohexane/ethyl acetate (90/10) to give a mixture of diastereoisomere cis-trans (50–50) of (2-methyl-4-prop-2-ynylamino-3,4-dihydro-2H-quinolin-1-yl)-phenyl-methanone (0.06 g, 17.6% yield).

後処理

  1. stirringThe reaction mixture was then stirred at room temperature for one hour
  2. stirringunder stirring
  3. filtrationThe desired compound was filtered
  4. customafter precipitation
  5. dissolutionThe compound was dissolved in ethyl acetate
  6. washwashed with water
  7. customThe organic layer was separated
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed
  10. customto give a brown oil which
  11. customwas purified by flash chromatography with cyclohexane/ethyl acetate (95/5) as eluent
  12. customcyclohexane/ethyl acetate (90/10) to give

出典と根拠

ORDレコード
ord-6a9ab8d930a44614a25a459cd3846235
出典データセット
uspto-grants-2007_05
特許番号
US07220760B2

反応ノート

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