Benzyloxyamine hydrochloride → 1-(Benzyloxyimino-methyl)-cyclopentanecarboxylic acid methyl ester

HRID 2055165ノート

反応式

HRID 2055165 の反応式
[CH3:1][O:2][C:3]([C:5]1([CH:10]=O)[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].C([O-])(=O)C.[Na+].Cl.[CH2:18]([O:25][NH2:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CO>[CH3:1][O:2][C:3]([C:5]1([CH:10]=[N:26][O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6][CH2:7][CH2:8][CH2:9]1)=[O:4]

参加物

5

反応物 3

HCID 102312Benzyloxyamine hydrochlorideHCID 517045Sodium AcetateHCID 10931680Methyl 1-formylcyclopentanecarboxylate

生成物 1

HCID 866064701-(Benzyloxyimino-methyl)-cyclopentanecarboxylic acid methyl ester収率 44%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 1-formyl-cyclopentanecarboxylic acid methyl ester (3.1 g, 19.8 mmol), sodium acetate (2.74 g, 39.72 mmol) and O-benzylhydroxylamine hydrochloride (6.34 g, 39.7 mmol) were stirred in methanol (120 mL) for 18 h. The methanol was removed in vacuo and the residue partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc (50 mL×2). The combined organic extracts were dried (MgSO4) and were evaporated in vacuo. Purification by flash column chromatography using an eluting system of hexane/EtOAc (95:5 to 90:10) provided the title compound as a clear colorless oil (2.26 g, 44%). MH+262.

後処理

  1. customThe methanol was removed in vacuo
  2. customthe residue partitioned between water and EtOAc
  3. extractionThe aqueous phase was extracted with EtOAc (50 mL×2)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customwere evaporated in vacuo
  6. customPurification by flash column chromatography

出典と根拠

ORDレコード
ord-0ba7c710b4a0491bb33e3f5043ea4866
出典データセット
uspto-grants-2008_02
特許番号
US07332485B2

反応ノート

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