Sodium cyanoborohydride → N-[2-(2,4-dichlorophenyl)-1-fluoromethyl-ethyl]-O-methyl-hydroxylamine

HRID 1039355노트

반응식

HRID 1039355 반응식
[CH3:1][O:2][N:3]=[C:4]([CH2:14][F:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13].C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:13][C:7]1[CH:8]=[C:9]([Cl:12])[CH:10]=[CH:11][C:6]=1[CH2:5][CH:4]([NH:3][O:2][CH3:1])[CH2:14][F:15]

참가 물질

4

반응물 2

HCID 5003444Sodium cyanoborohydrideHCID 866790801-(2,4-dichloro-phenyl)-3-fluoro-propan-2-one O-methyl-oxime

생성물 1

HCID 86679075N-[2-(2,4-dichlorophenyl)-1-fluoromethyl-ethyl]-O-methyl-hydroxylamine수율 76.5%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
23 °C

실험 절차

To a stirred solution of 1-(2,4-dichloro-phenyl)-3-fluoro-propan-2-one O-methyl-oxime (0.36 g; 1.4 mmol) in acetic acid (2.8 ml) was added portionwise sodium cyanoborohydride 95% (0.18 g; 2.8 mmol). The mixture was stirred for 18 hours at 23° C. Most of acetic acid was removed under reduced pressure. The residue was poured in water (10 ml) and was extracted with dichloromethane (3×10 ml). Combined organics were dried over sodium sulfate and solvent was removed in vacuo. The crude was subject to flash chromatography (eluant: c-hexane/ethyl acetate 95:5) to afford 0.27 g (75% of theory) of N-[2-(2,4-dichlorophenyl)-1-fluoromethyl-ethyl]-O-methyl-hydroxylamine as a yellow oil.

후처리

  1. customMost of acetic acid was removed under reduced pressure
  2. additionThe residue was poured in water (10 ml)
  3. extractionwas extracted with dichloromethane (3×10 ml)
  4. dry with materialCombined organics were dried over sodium sulfate and solvent
  5. customwas removed in vacuo

출처 및 근거

ORD 기록
ord-7d321086b7084af18ec09995f5bcebb3
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552049B2

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