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

HRID 32171노트

반응식

HRID 32171 반응식
[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]

참가 물질

8

반응물 5

HCID 176Acetic Acid2회HCID 6561Isobutyraldehyde2회HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2회HCID 231425251-[2-(3,3,4,4-Tetramethylcyclopent-1-enyl)phenyl]piperazine

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2d67f4498dad4ad49053518bd1a7461a
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425554B2

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