Sodium methanethiolate → tert-Butyl 4-((methylthio)methyl)piperidine-1-carboxylate

HRID 1894361ノート

反応式

HRID 1894361 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][S-:27].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][S:27][CH3:26])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

4

反応物 2

HCID 4378561Sodium methanethiolateHCID 106428511-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidine

生成物 1

HCID 21087276tert-Butyl 4-((methylthio)methyl)piperidine-1-carboxylate収率 98.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 4-(toluene-4-sulfonyloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (9.765 g, 26.43 mmol) in methanol (1 00mL) at room temperature was added sodium thiomethoxide (5.557 g, 79.29 mmol, Aldrich). The reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was taken in methylene chloride and washed with water (3×) and brine (1×). The organic layer was dried over anhydrous sodium sulfate and concentrated to give a clear oil as crude product of 4-methylsulfanylmethyl-piperidine-1-carboxylic acid tert-butyl ester (6.37 g).

後処理

  1. concentrationthen concentrated
  2. washwashed with water (3×) and brine (1×)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-417ca69b37364c94ae112a5df2ac1c7c
出典データセット
uspto-grants-2013_08
特許番号
US08513239B2

反応ノート

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