1,2-Dimethoxyethane → 4-[4-Methyl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester

HRID 32259

反応式

HRID 32259 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](OS(C(F)(F)F)(=O)=O)=[C:4]([CH:16]2[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:18]([CH3:25])([CH3:24])[CH2:17]2)[CH:3]=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH:37]=[C:36]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=2[CH:16]2[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:18]([CH3:25])([CH3:24])[CH2:17]2)[CH2:35][CH2:34]1)=[O:32])([CH3:27])([CH3:28])[CH3:29]

参加物

8

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 59769407Trifluoromethanesulfonic acid 4-methyl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl ester

生成物 1

HCID 597693754-[4-Methyl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester収率 63.3%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
90 °C

実験手順

To a mixture of trifluoromethanesulfonic acid 4-methyl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl ester (430 mg, 1.14 mmol) produced in Example (104d), 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (421 mg, 1.36 mmol) (Paul R. Eastwood, Tetrahedron Lett., 2000, 41, 3705) and 1,2-dimethoxyethane (20 mL) were added tetrakis(triphenylphosphine)palladium(0) (65 mg, 0.06 mmol) and 2N aqueous solution of sodium carbonate (1.72 mL, 3.41 mmol), followed by stirring for 8 hours at an external temperature of 90° C. under a nitrogen atmosphere. Brine was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the filtrate was concentrated to give a residue, which was purified by silica gel column chromatography (ethyl acetate/heptane) to give 297 mg of the title compound as a light yellow oil.

後処理

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. concentrationthe filtrate was concentrated
  3. customto give a residue, which
  4. customwas purified by silica gel column chromatography (ethyl acetate/heptane)

出典と根拠

ORDレコード
ord-2e59f4c5449b4413b0e6370be389ecb4
出典データセット
uspto-grants-2008_09
特許番号
US07425554B2

関連ノート

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