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

HRID 2055165노트

반응식

HRID 2055165 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 866064701-(Benzyloxyimino-methyl)-cyclopentanecarboxylic acid methyl ester수율 44%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0ba7c710b4a0491bb33e3f5043ea4866
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07332485B2

반응 노트

불러오는 중…