Imidazole → (S)-2-(tert-butyldimethylsilyloxy)-1-(pyrrolidin-1-yl)propan-1-one

HRID 2279467ノート

反応式

HRID 2279467 の反応式
[OH:1][C@@H:2]([CH3:10])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].N1C=CN=C1.[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17].O>CN(C1C=CN=CC=1)C.CN(C=O)C>[Si:20]([O:1][C@@H:2]([CH3:10])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21]

参加物

7

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 11051776(2S)-2-hydroxy-1-(1-pyrrolidinyl)-1-propanone

生成物 1

HCID 11807344(S)-2-(tert-butyldimethylsilyloxy)-1-(pyrrolidin-1-yl)propan-1-one収率 77.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 108 (41.1 g, 287.0 mmol), imidazole (29.31 g, 430.6 mmol), and DMAP (3.507 g, 28.70 mmol) in DMF (100 mL) was added slowly tert-butylchlorodimethylsilane (54.08 g, 358.8 mmol) and the reaction was stirred at RT for 18 h. Water was added and mixture was extracted with Et2O. The organic layer was dried, filtered, and concentrated. The resulting residue was purified by passing through a SiO2 plug eluting with an EtOAc/hexane gradient (10 to 50% EtOAc) to afford 56.93 g (77.04%) of (S)-2-(tert-butyldimethylsilyloxy)-1-(pyrrolidin-1-yl)propan-1-one (110).

後処理

  1. extractionmixture was extracted with Et2O
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified
  6. washeluting with an EtOAc/hexane gradient (10 to 50% EtOAc)

出典と根拠

ORDレコード
ord-2924cbacd0714900949f796d8899a9d2
出典データセット
uspto-grants-2015_09
特許番号
US09133187B2

反応ノート

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