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Sodium hydride → 3-Oxa-tricyclo[3.2.2.02,4]nonane-2-carboxylic acid N-(4-nitro-3-trifluoromethyl-phenyl)-hydrazide

HRID 1591703
ノート
印刷プレビュー

反応式

HRID 1591703 の反応式
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]23[O:21][CH:20]2[CH:19]2[CH2:22][CH2:23][CH:16]3[CH2:17][CH2:18]2)=[O:14])=[CH:8][C:7]=1[C:24]([F:27])([F:26])[F:25])([O-:5])=[O:4].C1(P([NH:42]O)(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C=O)C>[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:13]([C:15]23[O:21][CH:20]2[CH:19]2[CH2:18][CH2:17][CH:16]3[CH2:23][CH2:22]2)=[O:14])[NH2:42])=[CH:8][C:7]=1[C:24]([F:27])([F:25])[F:26])([O-:5])=[O:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 419256DiphenylphosphinylhydroxylamineHCID 235461863-Oxa-tricyclo[3.2.2.02,4] nonane-2-carboxylic acid (4-nitro-3-trifluoromethyl-phenyl)-amide

生成物 1

HCID 235461873-Oxa-tricyclo[3.2.2.02,4]nonane-2-carboxylic acid N-(4-nitro-3-trifluoromethyl-phenyl)-hydrazide収率 15.4%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
70 °C

実験手順

NaH (60% in mineral oil, 7.9 mg, 0.20 mmol, 1.4 eq) was added to the solution of 11E (50 mg, 0.14 mmol, 1 eq) in DMF (3 mL). The reaction mixture was heated at 70° C. for 2 h. The reaction was cooled to rt and diphenylphosphinylhydroxylamine (52 mg, 0.22 mmol, 1.6 eq, made according to the procedure of Colvin, E. W. et.al. Tetrahedron Lett. 23, 3835-6 (1982)) was added. The reaction mixture was stirred at rt overnight and quenched by addition of water (3 mL) and extracted with EtOAc (2×20 mL). The combined organics were washed with H2O (25 mL), dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with 10% EtOAc/CH2Cl2 gave 8.0 mg (0.022 mmol, 15.4%) of compound 11F as a yellow solid. HPLC conditions: 93% at 3.54 min (YMC S5 ODS 4.6×50 mm, 10%-90% aqueous methanol over 4 minute gradient with 0.2% H3PO4, detecting at 220 nm).

後処理

  1. temperatureThe reaction was cooled to rt
  2. addition23, 3835-6 (1982)) was added
  3. customquenched by addition of water (3 mL)
  4. extractionextracted with EtOAc (2×20 mL)
  5. washThe combined organics were washed with H2O (25 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography on silica gel eluting with 10% EtOAc/CH2Cl2

出典と根拠

ORDレコード
ord-83f1c18afb0c479996ad48ddb5a43549
出典データセット
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07291637B2

反応ノート

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