1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine → Tert-butyl 4-(methylthio)piperidine-1-carboxylate

HRID 473802ノート

反応式

HRID 473802 の反応式
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[CH3:19][S-:20].[Na+]>CO>[CH3:19][S:20][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]1

参加物

4

反応物 2

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 4378561Sodium methanethiolate

生成物 1

HCID 11053478Tert-butyl 4-(methylthio)piperidine-1-carboxylate収率 58.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (2.0 g, 7.2 mmol) and sodium thiomethoxide (1.0 g, 14.4 mmol) in methanol (30 mL) was refluxed for 15 h and then concentrated. The residue was partitioned between water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulfate, filtered and concentrated. Column chromatography on silica (3% ethyl acetate in hexanes) afforded tert-butyl 4-(methylthio)piperidine-1-carboxylate (0.98 g, 58% yield) as a colorless oil. MS (EI) for C11H21NO2S: 231 (M+).

後処理

  1. concentrationconcentrated
  2. customThe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washthe combined organic extracts washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-b9542cd363ec4ca29942888476db3072
出典データセット
uspto-grants-2014_01
特許番号
US08637499B2

反応ノート

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