Imidazole → 1-Benzyl-3-t-butyldimethylsilyloxymethylpyrrolidine

HRID 1090515

反応式

HRID 1090515 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 199149271-Benzyl-3-t-butyldimethylsilyloxymethylpyrrolidine収率 86.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0365be46c0de4d1d9a99df9035d38be2
出典データセット
uspto-grants-1992_01
特許番号
US05081237

関連ノート

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