Imidazole → 1-Benzyl-3-t-butyldimethylsilyloxymethylpyrrolidine

HRID 1650287

반응식

HRID 1650287 반응식
N1C=CN=C1.[CH2:6]([N:13]1[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].O>CN(C)C=O>[CH2:6]([N:13]1[CH2:17][CH2:16][CH:15]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 5176654(1-Benzylpyrrolidin-3-yl)methanol

생성물 1

HCID 199149271-Benzyl-3-t-butyldimethylsilyloxymethylpyrrolidine수율 86.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Imidazole (30.0 g) was added to a solution of 1-benzyl-3-hydroxymethylpyrrolidine (43.45 g) and t-butyldimethylsilyl chloride (48.5 g) in dimethylformamide(150 ml) under ice-cooling. The mixture was stirred at the same temperature for 2 hours and at ambient temperature for 15 hours. The mixture was poured into water (600 ml), extracted twice with ethyl acetate (200 ml and 100 ml), dried over magnesium sulfate and evaporated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (500 g) and eluted with a mixture of methanol and dichloromethane (5:95 V/V) to give 1-benzyl-3-t-butyldimethylsilyloxymethylpyrrolidine (60.15 g).

후처리

  1. temperaturecooling
  2. extractionextracted twice with ethyl acetate (200 ml and 100 ml)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto give a syrup
  6. washeluted with a mixture of methanol and dichloromethane (5:95 V/V)

출처 및 근거

ORD 기록
ord-b1b110a41d2545c9b1e7640b3290c306
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04923857

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