Cesium carbonate → (R)-4-[3-(tert-Butyldimethylsilanyloxy)-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

HRID 1986842ノート

反応式

HRID 1986842 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=[O:11])[CH2:2]1.Br[CH2:13][C@@H:14]([CH3:24])[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[Si:17]([O:16][CH2:15][C@H:14]([CH3:24])[CH2:13][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:1][CH2:2][C:3]1=[O:11])([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:18])[CH3:19]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 727572H-1,4-benzoxazin-3(4H)-oneHCID 11032834(S)-3-bromo-2-methylpropoxy-tert-butyldimethylsilane

生成物 1

HCID 68910127(R)-4-[3-(tert-Butyldimethylsilanyloxy)-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one収率 85%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A reaction flask was charged with 4H-Benzo[1,4]oxazin-3-one (1.49 g, 10.0 mmol), (S)-(3-bromo-2-methylpropoxy)-tert-butyldimethylsilane (2.67 g, 10.0 mmol), and Cs2CO3 (4.89 g, 15.0 mmol) in MeCN (15 mL) and stirred at rt for 7 days. The reaction mixture was quenched with water and the product extracted into EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 2:1) to give the title compound (2.84 g, 85%).

後処理

  1. customThe reaction mixture was quenched with water
  2. extractionthe product extracted into EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 2:1)

出典と根拠

ORDレコード
ord-0b27aa920bd943c4bd0c7dcb9ef6c920
出典データセット
uspto-grants-2009_06
特許番号
US07550459B2

反応ノート

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