HCID 19914911, 화합물 → HCID 19914940, 화합물

HRID 1090513노트

반응식

HRID 1090513 반응식
C([N:8]1[CH:12]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][CH2:10][CH:9]1[CH2:22][OH:23])C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[Si:15]([O:14][CH2:13][CH:12]1[NH:8][CH:9]([CH2:22][OH:23])[CH2:10][CH2:11]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

참가 물질

5

반응물 2

HCID 19914911HCID 19914911, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 19914940HCID 19914940, 화합물수율 86.8%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매

실험 절차

To a solution of 1-benzyl-5-t-butyldimethylsilyloxymethyl-2-hydroxymethylpyrrolidine (6.3 g) in methanol (63 ml) was added palladium hydroxide on carbon (630 mg) under nitrogen atmosphere. The apparatus was evacuated to remove nitrogen, then filled with hydrogen, and the mixture was stirred under hydrogen atmosphere until 19 mmol of hydrogen was absorbed. The palladium hydroxide on carbon was filtered off and the solvent was removed under reduced pressure to give 5-t-butyldimethylsilyloxymethyl-2-hydroxymethylpyrrolidine (4.0 g). To a solution of this residue in tetrahydrofuran (60 ml) and water (30 ml) were added sodium bicarbonate (4.10 g) and then allyl chloroformate (1.42 ml) at room temperature. After stirring for 2 hours, sodium bicarbonate (2.1 g) and allyloxycarbonyl chloride (1.42 ml) was added. After stirring for an hour, ethyl acetate (100 ml) and water (50 ml) were added and the aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate, water and brine successively, dried over magnesium sulfate and evaporated under reduced pressure. The residue was column chromatographed on silica gel (eluent: hexane/ethyl acetate, 9:1-4:1 V/V) to give 1-allyloxycarbonyl-5-t- butyldimethylsilyloxymethyl-2-hydroxymethylpyrrolidine (4.91 g).

후처리

  1. customThe apparatus was evacuated
  2. customto remove nitrogen
  3. additionfilled with hydrogen
  4. customwas absorbed
  5. filtrationThe palladium hydroxide on carbon was filtered off
  6. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-058e170c8235463594d535d3a6196805
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05081237

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