1,4-Dioxane → (S)-N-(2-hydroxy-1-phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 595789ノート

反応式

HRID 595789 の反応式
Br[C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][C@@H:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][OH:11])=[O:7])=[CH:4][CH:3]=1.[O:20]1CCO[BH:21]1.[CH:25]1(P(C2CCCCC2)C2CCCCC2)[CH2:30]CCC[CH2:26]1.[C:44]([O-:47])(=O)[CH3:45].[K+].O1CCOC[CH2:50]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:11][CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[C:5]1[CH:18]=[CH:19][C:2]([B:21]2[O:20][C:25]([CH3:30])([CH3:26])[C:44]([CH3:45])([CH3:50])[O:47]2)=[CH:3][CH:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

7

反応物 5

HCID 312751,4-DioxaneHCID 75806TricyclohexylphosphineHCID 517044Potassium AcetateHCID 5326306InChI=1/C2H5BO2/c1-2-5-3-4-1/h3H,1-2HHCID 113356449(S)-4-bromo-N-(2-hydroxy-1-phenylethyl)benzamide

生成物 1

HCID 123160895(S)-N-(2-hydroxy-1-phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
100 °C

実験手順

To a solution of (S)-4-bromo-N-(2-hydroxy-1-phenylethyl)benzamide, 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane (B2(PlN)2) (238 mg, 0.937 mmol), Pd2(dba)3 (21.45 mg, 0.023 mmol), tricyclohexylphosphine (19.71 mg, 0.070 mmol) in dioxane (1.562 mL) was added potassium acetate (138 mg, 1.405 mmol). The reaction mixture was degassed by N2 stream for 15 min. The reaction mixture was heated at 100° C. overnight. After diluted with EtOAc, the reaction mixture was filtered through Celite. After concentrated, (S)—N-(2-hydroxy-1-phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide was used for the next step without further purification. LCMS (m/z): 368.3 (MH+), 0.88 min (for boronic ester) and 286.1 (MH+), 0.49 min (for the corresponding boronic acid).

後処理

  1. customThe reaction mixture was degassed by N2 stream for 15 min
  2. additionAfter diluted with EtOAc
  3. filtrationthe reaction mixture was filtered through Celite
  4. concentrationAfter concentrated
  5. custom(S)—N-(2-hydroxy-1-phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide was used for the next step without further purification
  6. custom368.3 (MH+), 0.88 min (for boronic ester) and 286.1 (MH+), 0.49 min

出典と根拠

ORDレコード
ord-6098c9e485cb494493c2af9a6a9a169a
出典データセット
uspto-grants-2016_01
特許番号
US09242996B2

反応ノート

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