Tricyclohexylphosphine → tert-Butyl (4-cyclopropyl-2-methylphenyl)carbamate

HRID 2400275ノート

反応式

HRID 2400275 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([CH3:16])[CH:3]=1.O.[CH:18]1(B(O)O)[CH2:20][CH2:19]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH:18]1([C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([CH3:16])[CH:3]=2)[CH2:20][CH2:19]1

参加物

9

反応物 4

HCID 75806TricyclohexylphosphineHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 23074904N-Boc-4-iodo-2-methylanilineHCID 66762321Cyclopropylboronic acid monohydrate

生成物 1

HCID 86665748tert-Butyl (4-cyclopropyl-2-methylphenyl)carbamate収率 86.5%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of tert-butyl (4-iodo-2-methylphenyl)carbamate (1.04 g), cyclopropylboronic acid monohydrate (422 mg), palladium(II) acetate (35.1 mg), tricyclohexylphosphine (87.5 mg), tripotassium phosphate monohydrate (2.52 g), toluene (8.7 mL), and water (0.87 mL) was stirred at 100° C. for 15 hours. The reaction mixture was left to cool and then diluted with ethyl acetate and filtered through Celite (registered trademark). The filtrate was washed with brine and dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (668 mg). 1H-NMR (CDCl3) δ ppm: 0.55-0.70 (2H, m), 0.80-1.00 (2H, m), 1.51 (9H, s), 1.75-1.90 (1H, m), 2.21 (3H, s), 5.85-6.45 (1H, br), 6.75-7.00 (2H, m), 7.45-7.75 (1H, m).

後処理

  1. waitThe reaction mixture was left
  2. temperatureto cool
  3. filtrationfiltered through Celite (registered trademark)
  4. washThe filtrate was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-1badeb70f9d44589a8fd3ae977055fad
出典データセット
uspto-grants-2014_08
特許番号
US08796247B2

反応ノート

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