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

HRID 32240ノート

反応式

HRID 32240 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-008abb3b8bc84ee9a247d98b14dc0536
出典データセット
uspto-grants-2008_09
特許番号
US07425554B2

反応ノート

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