Acetic Acid → 1-Acetamido-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene

HRID 863521ノート

反応式

HRID 863521 の反応式
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[CH2:13][C:12](=O)[CH2:11][CH2:10]2)(=[O:3])[CH3:2].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C(O)(=O)C.C([BH3-])#N.[Na+]>C1C=CC=CC=1.CN(C=O)C.CC1C=CC(S(O)(=O)=O)=CC=1>[C:1]([NH:4][C:5]1[C:14]2[CH2:13][CH:12]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydrideHCID 134241118-Acetamido-2-tetralone

生成物 1

HCID 196962461-Acetamido-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene収率 69.7%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 19608675Benzene dimethylformamide溶媒

実験手順

A mixture of 8-acetamido-2-tetralone (0.4 g, 2 mmol), pyrrolidine (0.28 g, 4 mmol) and tosic acid (10 mg) in benzene:DMF (5:1, 12 mL) was heated at reflux with a Dean-Stark trap for 4 h. The solvent was evaporated and the residue dissolved in 1:1 MeOH:THF (10 mL). Acetic acid (1 mL) and sodium cyanoborohydride (0.25 g, 4 mmol) were added, and the reaction stirred for 16 h. The solvent was evaporated and the residue taken up in water:methylene chloride. The aqueous layer was basified with 12.5% NaOH, and back extracted. The combined organic phase was dried over sodium sulfate, filtered and evaporated. The residue solidified upon standing, and was crystallized from tolune:hexane to give the product (0.36 g).

後処理

  1. temperaturewas heated
  2. temperatureat reflux with a Dean-Stark trap for 4 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in 1:1 MeOH
  5. customThe solvent was evaporated
  6. extractionback extracted
  7. dry with materialThe combined organic phase was dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customwas crystallized from tolune

出典と根拠

ORDレコード
ord-fa30521bf41b4b8b86dac3d46a1e75a9
出典データセット
uspto-grants-1998_02
特許番号
US05721234

反応ノート

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