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Morpholine → 4-(4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl)morpholine

HRID 57519
ノート
印刷プレビュー

反応式

HRID 57519 の反応式
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[O:3]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.CCN(CC)CC>C(Cl)Cl.CCOC(C)=O.O>[O:44]1[CH2:45][CH2:46][N:41]([C:13]([C:12]2[CH:11]=[CH:10][C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:1])([CH3:18])[O:3]3)=[CH:17][CH:16]=2)=[O:15])[CH2:42][CH2:43]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 8083MorpholineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

生成物 1

HCID 27601414-(4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl)morpholine
収率 81%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 22728543Water ethylacetate溶媒

実験手順

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (200 mg, 0.806 mmol) in CH2Cl2 (10 mL) was subsequently added EDCl (232 mg, 1.21 mmol), HOBt (163 mg, 1.21 mmol), morpholine (0.11 mL, 1.21 mmol), and Et3N (0.22 mL, 1.61 mmol). The mixture was stirred at room temperature overnight, treated with EtOAc/H2O, and extracted with EtOAc. The combined extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography to give the title compound (207 mg, 81% yield). MS (m/z): 318 (M+H)+

後処理

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-bfb0987f2d5d40db82adaa469c290a0e
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09434726B2

反応ノート

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