Acetic Acid → (R)-1-butyl-4-[2-(4,4-diethylcyclohexyl)-4-(3-methoxypyrrolidin-1-yl)phenyl]piperazine

HRID 32240노트

반응식

HRID 32240 반응식
[CH2:1]([C:3]1([CH2:28][CH3:29])[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[C:13]([N:15]3[CH2:19][CH2:18][C@@H:17]([O:20][CH3:21])[CH2:16]3)[CH:12]=[CH:11][C:10]=2[N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:5][CH2:4]1)[CH3:2].[CH:30](=O)[CH2:31][CH2:32][CH3:33].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.O1CCCC1>[CH2:30]([N:25]1[CH2:24][CH2:23][N:22]([C:10]2[CH:11]=[CH:12][C:13]([N:15]3[CH2:19][CH2:18][C@@H:17]([O:20][CH3:21])[CH2:16]3)=[CH:14][C:9]=2[CH:6]2[CH2:7][CH2:8][C:3]([CH2:1][CH3:2])([CH2:28][CH3:29])[CH2:4][CH2:5]2)[CH2:27][CH2:26]1)[CH2:31][CH2:32][CH3:33]

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 261ButanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59769451(R)-1-[2-(4,4-diethylcyclohexyl)-4-(3-methoxypyrrolidin-1-yl)phenyl]piperazine

생성물 1

HCID 15605391(R)-1-butyl-4-[2-(4,4-diethylcyclohexyl)-4-(3-methoxypyrrolidin-1-yl)phenyl]piperazine수율 93.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

실험 절차

To a mixture of the crude product of (R)-1-[2-(4,4-diethylcyclohexyl)-4-(3-methoxypyrrolidin-1-yl)phenyl]piperazine produced in Example (98b) (160 mg), butyraldehyde (0.052 mL, 0.584 mmol) and tetrahydrofuran (7 mL) were added sodium triacetoxyborohydride (164 mg, 0.774 mmol) and acetic acid (0.022 mL, 0.384 mmol) in that order, followed by stirring for 1 hour at room temperature. Ethyl acetate and saturated aqueous solution of sodium hydrogencarbonate were added to the reaction mixture and extraction was performed with ethyl acetate. The separated organic layer was washed with brine and then dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 170 mg of (R)-1-butyl-4-[2-(4,4-diethylcyclohexyl)-4-(3-methoxypyrrolidin-1-yl)phenyl]piperazine as a light brown oil.

후처리

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-008abb3b8bc84ee9a247d98b14dc0536
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425554B2

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