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

HRID 32216ノート

反応式

HRID 32216 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[C:5]([CH:15]2[CH2:20][C:19]([CH3:22])([CH3:21])[CH2:18][C:17]([CH3:24])([CH3:23])[CH2:16]2)[CH:4]=1.C(O[BH-](O[C:35](=[O:37])[CH3:36])OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+].O1[CH2:52][CH2:51][CH2:50][CH2:49]1>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:49][CH:50]3[CH2:36][CH2:35][O:37][CH2:52][CH2:51]3)[CH2:11][CH2:10]2)=[C:5]([CH:15]2[CH2:20][C:19]([CH3:22])([CH3:21])[CH2:18][C:17]([CH3:24])([CH3:23])[CH2:16]2)[CH:4]=1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 231427891-[4-Methoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

生成物 1

HCID 112589191-[4-Methoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]-4-(tetrahydropyran-4-ylmethyl)piperazine

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1-[4-methoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine (10 mg, 0.030 mmol) produced in Example (85c) in tetrahydrofuran (1 mL) were added tetrahydropyranyl-4-carbaldehyde (5.2 mg, 0.045 mmol), sodium triacetoxyborohydride (13 mg, 0.061 mmol) and acetic acid (1.8 mg, 0.030 mmol) in that order, followed by stirring for 60 minutes at room temperature. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture, extraction was performed with ethyl acetate, and the organic layer was concentrated. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 1-[4-methoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenyl] -4-(tetrahydropyran-4-ylmethyl)piperazine.

後処理

  1. concentrationthe organic layer was concentrated
  2. 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-120bef8dcc08467f9e978ceb01bf104b
出典データセット
uspto-grants-2008_09
特許番号
US07425554B2

反応ノート

読み込み中…