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Trifluoroacetic acid → 1-Benzyloxycarbonyl-4(2-methylthiophenyl)piperidine

HRID 1108028
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HRID 1108028 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](O)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][CH3:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][CH3:24])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 187863061-Benzyloxycarbonyl-4-hydroxy-4-(2-methylthiophenyl)piperidine

생성물 1

HCID 111106201-Benzyloxycarbonyl-4(2-methylthiophenyl)piperidine수율 67.7%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

The product of Step 2 (5.1 g) in CH2Cl2 (50 mL) was treated sequentially with trifluoroacetic acid (8.9 mL) and triethylsilane (34.5 mL). After 18 h, the solution was treated with saturated NaHCO3 (150 mL). After a further 1 h, the organic layer was separated and the aqueous extracted with CH2Cl2 (100 mL). The organic extracts were combined, dried over Na2SO4, filtered and evaporated. The crude product was purified by silica gel chromatography, eluting with EtOAc/hexane mixtures to give 1-benzyloxycarbonyl-4(2-methylthiophenyl)piperidine (3.3 g).

후처리

  1. waitAfter a further 1 h
  2. customthe organic layer was separated
  3. extractionthe aqueous extracted with CH2Cl2 (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with EtOAc/hexane

출처 및 근거

ORD 기록
ord-4cb6fe4f100e44b4a103b7312aeb065d
출처 데이터셋
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06063926

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