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

HRID 350717ノート

反応式

HRID 350717 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.[Na].[CH3:20][SH:21]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH3:20][S:21][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

5

反応物 2

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 45051789Methylmercaptan sodium

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of tert-butyl 4-(methylsulfonyl)oxypiperidine-1-carboxylate (12.5 g), methylmercaptan sodium salt (3.31 g), tetra-n-butylammonium iodide (1.66 g) and tetrahydrofuran (50 mL) was stirred at room temperature for 72 hrs. The insoluble material was filtered through celite and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and tert-butyl 4-(methylthio)piperidine-1-carboxylate was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio) (6.89 g, yield 67%).

後処理

  1. filtrationThe insoluble material was filtered through celite
  2. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-5c841c5f7ea6479d82cc695701509b8b
出典データセット
uspto-grants-2007_02
特許番号
US07183276B2

反応ノート

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