Sodium Bicarbonate → HCID 68469403、化合物

HRID 387679ノート

反応式

HRID 387679 の反応式
Br[C:2]1[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:5]2[CH2:6][CH2:7][N:8]([CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[C:9](=[O:12])[C:10]=2[CH:11]=1.[C:24](=O)(O)[O-].[Na+]>O1CCOCC1.O.CN(C)C=O>[CH3:24][C:2]1[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:5]2[CH2:6][CH2:7][N:8]([CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[C:9](=[O:12])[C:10]=2[CH:11]=1

参加物

6

反応物 2

HCID 516892Sodium BicarbonateHCID 68473018HCID 68473018、化合物

生成物 1

HCID 68469403HCID 68469403、化合物

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

Added to a solution of 0.385 g of methyl 7-bromo-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate in 9.6 cm3 of dioxane, 2 cm3 of water and one drop of dimethylformamide, at a temperature close to 20° C., are 190 mg of sodium bicarbonate. The reaction medium is then degassed under an argon atmosphere, then 58 mg of methylboronic acid and 93 mg of tetrakis(triphenylphosphine)palladium are added. The mixture is heated at 150° C. in a microwave oven for 8 minutes, cooled to a temperature close to 20° C., filtered and concentrated to dryness under reduced pressure (5 kPa). The filtrate is taken up by 20 cm3 of dichloromethane and 10 cm3 of water. The organic phase is extracted, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure (5 kPa). The residual solution (around 4 cm3) is purified by flash chromatography over silica (column: 50 g; spherical silica of BP-SUP type, particle size: 20-40 μm; eluent: 80% heptane/20% ethyl acetate then 60% heptane/40% ethyl acetate then 100% ethyl acetate). After concentrating the fractions under reduced pressure, 35 mg of methyl 7-methyl-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate are obtained in the form of a colorless oil.

後処理

  1. customclose to 20° C.
  2. customThe reaction medium is then degassed under an argon atmosphere
  3. addition58 mg of methylboronic acid and 93 mg of tetrakis(triphenylphosphine)palladium are added
  4. temperaturecooled to a temperature
  5. customclose to 20° C.
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (5 kPa)
  8. extractionThe organic phase is extracted
  9. washwashed with a saturated aqueous solution of sodium chloride
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure (5 kPa)
  13. customThe residual solution (around 4 cm3) is purified by flash chromatography over silica (column
  14. concentrationAfter concentrating the fractions under reduced pressure, 35 mg of methyl 7-methyl-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate
  15. customare obtained in the form of a colorless oil

出典と根拠

ORDレコード
ord-4a2dca2aecc34a83ae38b28b5c9e1972
出典データセット
uspto-grants-2013_02
特許番号
US08372864B2

反応ノート

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