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

HRID 32216노트

반응식

HRID 32216 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  1. concentrationthe organic layer was concentrated
  2. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-120bef8dcc08467f9e978ceb01bf104b
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425554B2

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