Thiophenol → (3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide

HRID 627169ノート

反応式

HRID 627169 の反応式
[CH2:1]([O:4][N:5]([C@@H:18]1[C:23]([C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[CH:22][C@@H:21]([CH2:29][O:30][CH3:31])[NH:20][CH2:19]1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1>C(#N)C>[CH2:1]([O:4][NH:5][C@@H:18]1[C:23]([C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[CH:22][C@@H:21]([CH2:29][O:30][CH3:31])[NH:20][CH2:19]1)[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 89851925(3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide2 回

生成物 1

HCID 89852322(3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide収率 91%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of (3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide (Intermediate 141, 1.346 g, 2.96 mmol) and potassium carbonate (2.456 g, 17.77 mmol) in acetonitrile (50 mL) was added benzenethiol (1.825 mL, 17.77 mmol) and stirred at rt overnight. The solvent was evaporated then the crude mixture was redissolved in DCM and a little bit MeOH, filtered, loaded onto silica gel. The crude product was purified via flash chromatography (0-20% MeOH/DCM) and dried under high-vacuum to obtain the desired product (0.725 g, 91%) as a pale yellow oil.

後処理

  1. customThe solvent was evaporated
  2. dissolutionthe crude mixture was redissolved in DCM
  3. filtrationa little bit MeOH, filtered
  4. customThe crude product was purified via flash chromatography (0-20% MeOH/DCM)
  5. customdried under high-vacuum

出典と根拠

ORDレコード
ord-089c902999b34e3c89b581ca21f6656f
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

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