Formaldehyde → N-methyl-O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine

HRID 1895924노트

반응식

HRID 1895924 반응식
C=O.[F:3][C:4]([F:23])([F:22])[C:5]1[CH:6]=[C:7]([S:11]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][NH2:21])[CH2:16][CH2:15]2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1.[C:24](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[CH3:24][NH:21][O:20][CH:17]1[CH2:16][CH2:15][N:14]([S:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:4]([F:3])([F:22])[F:23])[CH:6]=2)(=[O:13])=[O:12])[CH2:19][CH2:18]1

참가 물질

6

반응물 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67118429O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine

생성물 1

HCID 86652730N-methyl-O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine수율 60%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

Formaldehyde (166 mg, 5.55 mmol) was added to a solution of O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl) hydroxylamine (200 mg, 0.617 mmol) in 1,2-dichlorethane (5 ml) and stirred at room temperature for 3 hours. Sodium triacetoxyborohydride was added and stirred at room temperature for 12 hours. The reaction mixture was diluted with of ethyl acetate (30 ml), washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (the residue was purified by preparative TLC (ethyl acetate/petroleum ether: 67/33) to give N-methyl-O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine (125 mg, 60%) as a white solid.

후처리

  1. stirringstirred at room temperature for 12 hours
  2. washwashed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (the residue
  7. customwas purified by preparative TLC (ethyl acetate/petroleum ether: 67/33)

출처 및 근거

ORD 기록
ord-4f729bacced04571841a441f23c72af3
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518934B2

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