Formaldehyde → (1-Methylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate

HRID 62681노트

반응식

HRID 62681 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:23])[O:17][CH2:18][CH:19]1[CH2:22][NH:21][CH2:20]1)([O-:3])=[O:2].[CH2:24](Cl)Cl.C=O.C([BH3-])#N.[Na+]>CC#N>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:23])[O:17][CH2:18][CH:19]1[CH2:20][N:21]([CH3:24])[CH2:22]1)([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 71007325Azetidin-3-ylmethyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate

생성물 1

HCID 71007324(1-Methylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate수율 75%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of azetidin-3-ylmethyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate (0.09 g, 0.26 mmol, 1.0 eq.) in CH3CN:CH2Cl2 was added aq. formaldehyde (0.77 mmol, 3.0 eq.). The reaction mixture was stirred at room temperature for 30 min then cooled to 0° C. Sodium cyanoborohydride (0.03 g, 0.46 mmol, 1.8 eq.) was added slowly. The reaction was quenched with an aqueous saturated solution of sodium bicarbonate. The product was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 5% MeOH/CH2Cl2) to obtain (1-methylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate (0.07 g, 75% yield).

후처리

  1. temperaturethen cooled to 0° C
  2. customThe reaction was quenched with an aqueous saturated solution of sodium bicarbonate
  3. extractionThe product was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (silica gel, 5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-000df2b28adc46eda198278cacdeb8a8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447030B2

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