Triethylamine → HCID 22851231、化合物

HRID 1463783ノート

反応式

HRID 1463783 の反応式
[CH2:1]([O:8][CH2:9][C@@H:10]([O:13][CH2:14][P:15]([O:21][CH:22]([CH3:24])[CH3:23])([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11]I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[H][H]>CO.[Pd]>[CH2:1]([O:8][CH2:9][C@@H:10]([O:13][CH2:14][P:15]([O:21][CH:22]([CH3:24])[CH3:23])([O:17][CH:18]([CH3:19])[CH3:20])=[O:16])[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 22851228(R)-1-(benzyloxy)-2-[(diisopropylphosphono)methoxy]-3-iodopropaneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 22851231HCID 22851231、化合物収率 94%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A solution of (R)-1-(benzyloxy)-2-[(diisopropylphosphono)methoxy]-3-iodopropane (12.0 g, 25.5 mmol) in 15 mL of methanol was treated with triethylamine (3.10 g, 30.6 mmol) and 10% palladium on carbon (2.0 g), and the mixture was placed under 40 psi hydrogen atmosphere in a Parr shaker apparatus. After 2 hours, the reaction mixture was filtered through a 1" pad of Celite, and the collected solid was washed with methanol. The filtrate was concentrated and treated with ethyl acetate (200 mL). The precipitate was removed by filtration, the filtrate was concentrated in vacuo, and the residue was purified by column chromatography on silica gel (10:1, 75% ethyl acetate/hexane) to afford 8.24 g (94%) of the title compound as a clear, colorless oil.

後処理

  1. filtrationthe reaction mixture was filtered through a 1" pad of Celite
  2. washthe collected solid was washed with methanol
  3. concentrationThe filtrate was concentrated
  4. additiontreated with ethyl acetate (200 mL)
  5. customThe precipitate was removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified by column chromatography on silica gel (10:1, 75% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-45a3accc2d784cc7be525a08959560a6
出典データセット
uspto-grants-1994_04
特許番号
US05302585

反応ノート

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