Glutaraldehyde → 9-Benzyl-9-azabicyclo[3.3.1]nonan-3-one

HRID 1939969ノート

反応式

HRID 1939969 の反応式
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH:5]=[O:6].[CH2:8]([C:15](O)=O)[C:9](CC(O)=O)=O.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>Cl>[CH2:18]([N:25]1[CH:3]2[CH2:2][CH2:1][CH2:15][CH:8]1[CH2:9][C:5](=[O:6])[CH2:4]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 3485GlutaraldehydeHCID 7504BenzylamineHCID 68328Acetonedicarboxylic acid

生成物 1

HCID 4195319-Benzyl-9-azabicyclo[3.3.1]nonan-3-one収率 33%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

To a 1 L round-bottomed flask equipped with a condenser and nitrogen inlet were added 80 g (0.2 mol) of a 25% aqueous solution of glutaraldehyde, 29.2 g (0.2 mol) 1,3-acetonedicarboxylic acid, and 11.4 g (0.2 mol) benzylamine. After the initial reaction had subsided, the pH was adjusted to 5 and maintained for 14 hours. The reaction was then taken up in 6N HCl, washed with ethyl acetate, and basified with 6N sodium hydroxide solution. The aqueous layer was extracted with methylene chloride, and the organic layer filtered through diatomaceous earth (Celite [trademark]) and evaporated. The residue was chromatographed on silica gel with ethyl acetate/methylene chloride as eluent to afford 15.034 g (33%) of a pale orange solid, mp 70-73C.

後処理

  1. customTo a 1 L round-bottomed flask equipped with a condenser and nitrogen inlet
  2. customAfter the initial reaction
  3. temperaturemaintained for 14 hours
  4. washwashed with ethyl acetate
  5. extractionThe aqueous layer was extracted with methylene chloride
  6. filtrationthe organic layer filtered through diatomaceous earth (Celite [trademark])
  7. customevaporated
  8. customThe residue was chromatographed on silica gel with ethyl acetate/methylene chloride as eluent

出典と根拠

ORDレコード
ord-12e97f8d13e14c29a41a8f782b518aef
出典データセット
uspto-grants-1997_12
特許番号
US05698568

反応ノート

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