Methyl iodide → Tert-butyl 4-methyl-4-(methylthio)piperidine-1-carboxylate

HRID 524912ノート

反応式

HRID 524912 の反応式
[CH3:1][C:2]1([SH:15])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Li+].[CH3:17][Si]([N-][Si](C)(C)C)(C)C.CI>C1COCC1>[CH3:1][C:2]1([S:15][CH3:17])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 71629631tert-Butyl 4-mercapto-4-methylpiperidine-1-carboxylate

生成物 1

HCID 86720965Tert-butyl 4-methyl-4-(methylthio)piperidine-1-carboxylate収率 96.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of tert-butyl 4-methyl-4-sulfanyl-piperidine-1-carboxylate (380 mg, 1.642 mmol) in THF (5 mL) cooled to −78° C. was added LiHMDS (1.724 mL of 1 M, 1.724 mmol) and the solution stirred for 10 mins before MeI (256.3 mg, 0.1124 mL, 1.806 mmol) was added and the solution allowed to warm to 0° C. over approximately 1 h. The reaction was then quenched carefully by the addition of saturated ammonium chloride and extracted into EtOAc. The aqueous was further extracted with EtOAc and the combined organics were washed with brine, dried (MgSO4) and concentrated to give a yellow oil (390 mg, 96%).

後処理

  1. additionwas added
  2. customThe reaction was then quenched carefully by the addition of saturated ammonium chloride
  3. extractionextracted into EtOAc
  4. extractionThe aqueous was further extracted with EtOAc
  5. washthe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-459917c0919c488ea286fe7c65a8439b
出典データセット
uspto-grants-2016_05
特許番号
US09340546B2

反応ノート

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