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

HRID 2218817ノート

反応式

HRID 2218817 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-6304cff4f74f40c9bddc182159f8bdc8
出典データセット
uspto-grants-2008_08
特許番号
US07410971B2

反応ノート

読み込み中…