Acetic Anhydride → 3-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl Acetate

HRID 1626129ノート

反応式

HRID 1626129 の反応式
[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1.[C:12]([O:15]C(=O)C)(=[O:14])[CH3:13]>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([O:15][C:12](=[O:14])[CH3:13])[CH2:7][CH2:8][C:9]=2[CH:10]=1

参加物

3

反応物 2

HCID 7918Acetic AnhydrideHCID 580828393-Chloro-6,7-dihydro-5h-cyclopenta[b]pyridine 1-oxide

生成物 1

HCID 580827683-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl Acetate

実験手順

A solution of 3-chloro-6,7-dihydro-5H-[1]pyrindine 1-oxide (2.07 g, 12.2 mmol) in acetic acid anhydride (62.2 ml, 659 mmol) was stirred at 110° C. for 20 hours. For the workup, the solvent was removed at reduced pressure and the residue quenched with saturated aqueous solution of sodium hydrogen carbonate. The aqueous phase was extracted with dichloromethane, the resulting organic layers combined and dried over sodium sulphate. After evaporation of the solvent, the residue was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 70:30 as the eluent. The acetic acid 3-chloro-6,7-dihydro-5H-[1]pyrindin-7-yl ester was obtained as a red liquid (1.57 g, 61% yield). MS (ISP): m/z=212 [M+H]+.

後処理

  1. customFor the workup, the solvent was removed at reduced pressure
  2. customthe residue quenched with saturated aqueous solution of sodium hydrogen carbonate
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. dry with materialdried over sodium sulphate
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 70:30 as the eluent

出典と根拠

ORDレコード
ord-29dcf8eb214f42309180d128712792da
出典データセット
uspto-grants-2014_07
特許番号
US08785436B2

反応ノート

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