Acetic Acid → 1-Cyclopentyl-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

HRID 32164

反応式

HRID 32164 の反応式
[CH3:1][C:2]1([CH3:22])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:3]1.[C:23]1(=O)[CH2:27][CH2:26][CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH:23]1([N:19]2[CH2:18][CH2:17][N:16]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH:4]3[CH2:3][C:2]([CH3:22])([CH3:1])[CH2:7][C:6]([CH3:8])([CH3:9])[CH2:5]3)[CH2:21][CH2:20]2)[CH2:27][CH2:26][CH2:25][CH2:24]1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 119922841-[2-(3,3,5,5-Tetramethylcyclohexyl)phenyl]piperazine

生成物 1

HCID 231416491-Cyclopentyl-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 1-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine (25 mg, 0.0832 mmol) produced in Example (8b), cyclopentanone (9.1 mg, 0.108 mmol), sodium triacetoxyborohydride (33.5 mg, 0.158 mmol) and acetic acid (0.009 mL, 0.158 mmol) was stirred for 1 hour and 40 minutes 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 organic layer was concentrated to produce a residue, which was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 1-cyclopentyl-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine as a colorless oil. δ: 0.92 (s, 6H), 1.13 (s, 6H), 1.16-1.36 (m, 6H), 1.39-1.51 (m, 4H), 1.66-1.76 (m, 2H), 1.86-1.96 (m, 2H), 2.48-2.58 (m, 1H), 2.67 (brs, 4H), 2.89-2.98 (m, 4H), 3.52-3.61 (m, 1H), 7.04-7.14 (m, 3H), 7.21 (d, J=8.8 Hz, 1H).

後処理

  1. concentrationThe organic layer was concentrated
  2. customto produce a residue, which
  3. customwas purified by NH silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-f7cec2cd12ba4e52b0f7a2ba31ebc45d
出典データセット
uspto-grants-2008_09
特許番号
US07425554B2

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