Potassium Phosphate, Tribasic → tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate

HRID 923456

反応式

HRID 923456 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)([CH3:4])([CH3:3])[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:25]1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)[CH2:30]CCC[CH2:26]1.C(/B(O)O)=C/C>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].O.O1CCOCC1>[CH:26](/[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][NH:7][C:6](=[O:16])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:25]/[CH3:30]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 5355539(Z)-Prop-1-en-1-ylboronic acidHCID 70183002-Bromo-N-(tert-butoxycarbonyl)benzylamineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

生成物 1

HCID 118318066tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate収率 648.7%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A mixed liquid of 1.50 g of tert-butyl(2-bromobenzyl)carbamate, 3.90 g of tripotassium phosphate, 348 mg of dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, 195 mg of tris(dibenzylideneacetone)dipalladium(0), 905 mg of (1Z)-prop-1-en-1-yl boronic acid, 30 ml of 1,4-dioxane, and 7.5 ml of water was stirred at 90° C. for 15 hours. The reaction mixture was left to be cooled to room temperature and then filtrated over Celite. The filtrate was concentrated under reduced pressure, and then to the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography to obtain 1.36 g of tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate.

後処理

  1. waitThe reaction mixture was left
  2. filtrationfiltrated over Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionto the reaction mixture was added water
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materiala saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate
  8. customthe solvent was then evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-ec9a003cbe024598972d82f1b2c6d7b6
出典データセット
uspto-grants-2016_03
特許番号
US09278968B2

関連ノート

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