tert-Butanol → 1-Benzyl-4-(N-Boc-amino)piperidine

HRID 555346ノート

反応式

HRID 555346 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C)(C)C.[C:20]([O:24][C:25](OC([O-])=O)=[O:26])([CH3:23])([CH3:22])[CH3:21]>[OH-].[Na+]>[C:20]([O:24][C:25](=[O:26])[NH:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1)([CH3:23])([CH3:22])[CH3:21]

参加物

5

反応物 3

HCID 6386tert-ButanolHCID 4158521-Benzyl-4-piperidylamineHCID 22064466Tert-butyldicarbonate

生成物 1

HCID 44386181-Benzyl-4-(N-Boc-amino)piperidine収率 82.8%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

1-Benzylpiperidin-4-ylamine (3 g, 15.8 mmol), the starting material, was dissolved in 1M aqueous sodium hydroxide solution (35.8 ml) and t-butanol (32 ml) in a 250 ml vessel, and t-butyl-dicarbonate ((t-Boc)2O; 3.79 g, 17.38 mmol) was added thereto while stirring, and the resulting mixture was reacted at room temperature for 12 hrs. After the completion of reaction, the reaction mixture was extracted with ethyl acetate twice. Then, the organic layer was washed with 0.1N hydrochloric acid solution and brine in order, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue thus obtained was purified with a silica gel column chromatography to obtain 3.80 g of the title compound as a white solid (82.8%).

後処理

  1. customthe resulting mixture was reacted at room temperature for 12 hrs
  2. customAfter the completion of reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate twice
  4. washThen, the organic layer was washed with 0.1N hydrochloric acid solution and brine in order
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified with a silica gel column chromatography

出典と根拠

ORDレコード
ord-1bc73f53efec4300b220744484a65aea
出典データセット
uspto-grants-2011_11
特許番号
US08053435B2

反応ノート

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