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Imidazole → 1-(Benzyloxycarbonyl)-3-(tert-butyldimethylsilyloxymethyl)piperidine

HRID 602123
ノート
印刷プレビュー

反応式

HRID 602123 の反応式
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH2:27][CH:26]([CH2:30][OH:31])[CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH2:27][CH:26]([CH2:30][O:31][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])[CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 2776577Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate

生成物 1

HCID 589926311-(Benzyloxycarbonyl)-3-(tert-butyldimethylsilyloxymethyl)piperidine収率 99%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

Imidazole (3.00 g, 44.0 mmol) and tert-butyldimethylsilyl chloride (6.63 g, 44.0 mmol) were added to 1-(benzyloxycarbonyl)piperidin-3-yl methanol (9.15 g, 36.7 mmol) in N,N-dimethylformamide (40 mL). The solution was stirred at room temperature for 6 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract washed with brine and was dried over magnesium sulfate, followed by evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 13.2 g (99%) of the desired compound as a colorless oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract washed with brine
  3. dry with materialwas dried over magnesium sulfate
  4. customfollowed by evaporation of the solvent
  5. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1)

出典と根拠

ORDレコード
ord-cb168814464c40849f6e4caa3ca11a9f
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07902367B2

反応ノート

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