Pyridine → Tert-butyl 3-[(4-nitrophenyl)sulfonyloxy]piperidine-1-carboxylate

HRID 1948915

반응식

HRID 1948915 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH:14][CH:15]1[CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]1.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]2)(=[O:12])=[O:11])=[CH:8][CH:9]=1)([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 74044-Nitrobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 5456991-Boc-3-hydroxypiperidine

생성물 1

HCID 86600822Tert-butyl 3-[(4-nitrophenyl)sulfonyloxy]piperidine-1-carboxylate수율 88.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-Nitrobenzenesulfonyl chloride (4.4 g) was added to a stirred solution of tert-butyl 3-hydroxypiperidine-1-carboxylate (4.0 g) and pyridine (2.25 ml) in methylene chloride (80 ml) and stirred at ambient temperature for 16 hours. The reaction mixture was poured into saturated sodium bicarbonate solution. The organic layer was separated, washed with brine and dried over sodium sulfate. The solution was evaporated under vacuum and triturated with diethylether and filtered to remove undesired solids. The diethylether liquors were evaporated under vacuum and dissolved in methylene chloride before purification by column chromatography on silica eluting with ethyl acetate/isohexane (20/80). The fractions containing the expected product were combined and evaporated under vacuum to give tert-butyl 3-[(4-nitrophenyl)sulfonyloxy]piperidine-1-carboxylate as a yellow crystalline solid (6.77 g); 1H NMR Spectrum: (CDCl3) 1.43 (s, 9H), 1.40-1.54 (m, 1H), 1.70-1.94 (m, 3H), 3.22-3.60 (m, 4H), 4.67 (m, 1H), 8.11 (s, 2H), 8.40 (s, 2H).

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solution was evaporated under vacuum
  5. customtriturated with diethylether
  6. filtrationfiltered
  7. customto remove undesired solids
  8. customThe diethylether liquors were evaporated under vacuum
  9. dissolutiondissolved in methylene chloride before purification by column chromatography on silica eluting with ethyl acetate/isohexane (20/80)
  10. additionThe fractions containing the expected product
  11. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-4618875084534497b107f5a213948a6f
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399667B2

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