Acetic Acid → 1-Isobutyl-4-[2-(3,3,4,4-tetramethylcyclopent-1-enyl)phenyl]piperazine

HRID 32171ノート

反応式

HRID 32171 の反応式
[CH3:1][C:2]1([CH3:21])[C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:3]1.[CH:22](=O)[CH:23]([CH3:25])[CH3:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:22]([N:18]1[CH2:17][CH2:16][N:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:4]2[CH2:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:21])([CH3:1])[CH:3]=2)[CH2:20][CH2:19]1)[CH:23]([CH3:25])[CH3:24]

参加物

8

反応物 5

HCID 176Acetic Acid2 回HCID 6561Isobutyraldehyde2 回HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2 回HCID 231425251-[2-(3,3,4,4-Tetramethylcyclopent-1-enyl)phenyl]piperazine

生成物 1

HCID 113597681-Isobutyl-4-[2-(3,3,4,4-tetramethylcyclopent-1-enyl)phenyl]piperazine収率 18%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of the 1-[2-(3,3,4,4-tetramethylcyclopent-1-enyl)phenyl]piperazine (20 mg, 0.0703 mmol) produced in Example (54d) in tetrahydrofuran (1 mL) were added isobutyraldehyde (6.6 mg, 0.0914 mmol), sodium triacetoxyborohydride (19.4 mg, 0.0914 mmol) and acetic acid (0.0076 mL, 0.134 mmol), followed by stirring for 4 hours at room temperature. After further adding isobutyraldehyde (6.6 mg, 0.0914 mmol), sodium triacetoxyborohydride (19.4 mg, 0.0914 mmol) and acetic acid (0.0076 mL, 0.134 mmol) to the mixture, stirring was continued for 3 hours at room temperature. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed three times with ethyl acetate. The obtained organic layers were concentrated and the resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 4.3 mg of 1-isobutyl-4-[2-(3,3,4,4-tetramethylcyclopent-1-enyl)phenyl]piperazine as a colorless oil.

後処理

  1. stirringstirring
  2. waitwas continued for 3 hours at room temperature
  3. concentrationThe obtained organic layers were concentrated
  4. customthe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

出典と根拠

ORDレコード
ord-2d67f4498dad4ad49053518bd1a7461a
出典データセット
uspto-grants-2008_09
特許番号
US07425554B2

反応ノート

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