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

HRID 627169노트

반응식

HRID 627169 반응식
[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]

참가 물질

5

반응물 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 89851925(3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide2회

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-089c902999b34e3c89b581ca21f6656f
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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