Potassium Phosphate, Tribasic → HCID 57978234、化合物

HRID 1866540

反応式

HRID 1866540 の反応式
[C:1]([N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][CH:10]=[CH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].B1(B2C3CCCC2CCC3)C2CCCC1CCC2.Br[C:38]1[CH:39]=[CH:40][C:41]2[O:45][CH:44]([CH2:46][CH3:47])[CH2:43][C:42]=2[CH:48]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1>[C:15]([O:14][C:12]([N:8]([CH2:9][CH2:10][CH2:11][C:38]1[CH:39]=[CH:40][C:41]2[O:45][CH:44]([CH2:46][CH3:47])[CH2:43][C:42]=2[CH:48]=1)[C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])=[O:13])([CH3:18])([CH3:17])[CH3:16]

参加物

9

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 10244201N,N-Bis-Boc-N-allylamineHCID 113224419-Borabicyclo[3.3.1]nonane dimerHCID 57978247HCID 57978247、化合物

生成物 1

HCID 57978234HCID 57978234、化合物収率 46%

試薬・触媒・溶媒 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

N,N-Bis-Boc-N-allylamine (2.99 g, 11.6 mmol) was azeotroped with toluene (2×50 mL) then dissolved in tetrahydrofuran (12 mL). The solution was cooled to 0° C., 9-borabicyclo[3.3.1]nonane dimer (0.5M in tetrahydrofuran, 46.5 mL, 23.2 mmol) was added and the mixture was stirred at 0° C. for 3 hours. A mixture of 5-bromo-2-ethyl-2,3-dihydro-benzofuran (preparation 98, enantiomer 2), (2.9 g, 12.8 mmol), tripotassium phosphate (7.7 mL, 23.2 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride (4.74 mg, 0.58 mmol) in N,N-dimethylformamide (12 mL) was added and the reaction mixture was stirred at room temperature for 18 hours. The reaction was then quenched with 2M sodium hydroxide solution (30 mL) and water (10 mL) and stirred for 1 hour at room temperature. The mixture was then extracted with diethyl ether, dried over magnesium sulfate and concentrated in vacuo. The residue was suspended in ethyl acetate:petroleum ether, 25:75, filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate:petroleum ether, 7:93, to afford the title compound as a clear oil in 46% yield, 2.15 g.

後処理

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature for 18 hours
  3. customThe reaction was then quenched with 2M sodium hydroxide solution (30 mL) and water (10 mL)
  4. stirringstirred for 1 hour at room temperature
  5. extractionThe mixture was then extracted with diethyl ether
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. filtrationpetroleum ether, 25:75, filtered
  9. concentrationthe filtrate was concentrated in vacuo
  10. customThe residue was purified by column chromatography on silica gel
  11. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-4a7c3556f9f940cc8dfbd23271ca82ba
出典データセット
uspto-grants-2009_12
特許番号
US07629358B2

関連ノート

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