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

HRID 1895924ノート

反応式

HRID 1895924 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4f729bacced04571841a441f23c72af3
出典データセット
uspto-grants-2013_08
特許番号
US08518934B2

反応ノート

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