(Diethylamino)sulfur trifluoride → Tert-butyl 3-cyano-3-(fluoromethyl)azetidine-1-carboxylate

HRID 217428

반응식

HRID 217428 반응식
[C:1]([C:3]1([CH2:14]O)[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1)#[N:2].CCN(S(F)(F)[F:22])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([C:3]1([CH2:14][F:22])[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1)#[N:2]

참가 물질

5

반응물 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 584389531,1-Dimethylethyl 3-cyano-3-(hydroxymethyl)-1-azetidinecarboxylate

생성물 1

HCID 58293513Tert-butyl 3-cyano-3-(fluoromethyl)azetidine-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

tert-Butyl 3-cyano-3-(hydroxymethyl)azetidine-1-carboxylate (5.0 g) was dissolved in DCM (100 mL). At 0° C., DAST (3.74 mL) was added thereto, followed by stirring at 0° C. for 3 hours. Three hours later, to the reaction liquid was added an aqueous NaHCO3 solution (100 mL), followed by extraction with DCM (50 mL) three times. The organic layer was washed with brine, dried over MgSO4, and then concentrated. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 50:50) to obtain tert-butyl 3-cyano-3-(fluoromethyl)azetidine-1-carboxylate (1.24 g) as a brown solid.

후처리

  1. customThree hours later, to the reaction liquid
  2. extractionfollowed by extraction with DCM (50 mL) three times
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 50:50)

출처 및 근거

ORD 기록
ord-3a948117613649c2a92702f858a50e0a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193378B2

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