Triethylamine → HCID 22851231, 화합물

HRID 1463783노트

반응식

HRID 1463783 반응식
[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

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 22851228(R)-1-(benzyloxy)-2-[(diisopropylphosphono)methoxy]-3-iodopropaneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 22851231HCID 22851231, 화합물수율 94%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-45a3accc2d784cc7be525a08959560a6
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05302585

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