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

HRID 1948915ノート

反応式

HRID 1948915 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4618875084534497b107f5a213948a6f
出典データセット
uspto-grants-2013_03
特許番号
US08399667B2

反応ノート

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