Trifluoroacetic acid → benzyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 385815노트

반응식

HRID 385815 반응식
[F:1][C:2]([F:21])([F:20])[S:3]([O:6][C:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])(C)C)=[O:14])[CH2:9][CH:8]=1)(=[O:5])=[O:4].FC(F)(F)C(O)=O.C(N(CC)CC)C.ClC(OC[C:41]1[CH:46]=[CH:45]C=[CH:43][CH:42]=1)=O>ClCCl>[F:21][C:2]([F:1])([F:20])[S:3]([O:6][C:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:19]2[CH:45]=[CH:46][CH:41]=[CH:42][CH:43]=2)=[O:14])[CH2:9][CH:8]=1)(=[O:4])=[O:5]

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

생성물 1

HCID 11303044benzyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Into a 50 mL roundbottom flask, was placed tert-butyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (3.5 g, 10.00 mmol). To this was added dichloromethane (20 mL) followed by the addition of trifluoroacetic acid (5 mL). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at room temperature. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. This was followed by the addition of dichloromethane (20 mL). This was followed by the addition of triethylamine (3.03 g, 29.94 mmol). To the mixture was added benzyl chloroformate (2.05 g, 12.02 mmol). The resulting solution was allowed to react overnight at room temperature. The reaction mixture was filtered and the filtrate was concentrated under vacuo. The crude mixture was purified by silica gel chromatography (1:40 EtOAc/petroleum ether) to yield the title compound as a yellow liquid.

후처리

  1. customInto a 50 mL roundbottom flask, was placed
  2. customto react
  3. concentrationThe mixture was concentrated by evaporation under vacuum
  4. customa rotary evaporator
  5. additionThis was followed by the addition of dichloromethane (20 mL)
  6. customto react overnight at room temperature
  7. filtrationThe reaction mixture was filtered
  8. concentrationthe filtrate was concentrated under vacuo
  9. customThe crude mixture was purified by silica gel chromatography (1:40 EtOAc/petroleum ether)

출처 및 근거

ORD 기록
ord-2a32d75af77741d8a5880a5a4860d506
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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