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Water → tert-Butyl 3-fluoro-4-oxoazepane-1-carboxylate

HRID 876418
ノート
印刷プレビュー

反応式

HRID 876418 の反応式
[F:1][CH:2]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][CH:4](C(OCC)=O)[C:3]1=[O:21].O.[Li+].[Cl-]>CS(C)=O>[F:1][CH:2]1[C:3](=[O:21])[CH2:4][CH2:5][CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 67230662644982-11-6

生成物 1

HCID 53415294tert-Butyl 3-fluoro-4-oxoazepane-1-carboxylate収率 21%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
125 °C

実験手順

The product from Step A was dissolved in DMSO (200 mL) and H2O (8.29 g, 460 mmol) followed by addition of LiCl (19.5 g, 460 mmol). The solution was warmed to 125° C. and the mixture was stirred overnight. The mixture was cooled to ambient temperature and partitioned between EtOAc (2.5 L) and water:brine (1:1, 2.0 L). The mixture was filtered through activated charcoal over Celite, which was washed with EtOAc, forming visible layers. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (10 to 80% EtOAc/hexanes) providing 4.5 g (21%) of the product as a thick pale orange oil.

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between EtOAc (2.5 L) and water:brine (1:1, 2.0 L)
  3. filtrationThe mixture was filtered through activated charcoal over Celite, which
  4. washwas washed with EtOAc
  5. customforming visible layers
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (10 to 80% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-f927669aee73420db3c90821f3d43d22
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08987251B2

反応ノート

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