Water → Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

HRID 1394328ノート

反応式

HRID 1394328 の反応式
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25].O>O1CCCC1>[CH3:23][S:24]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)(=[O:26])=[O:25]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

生成物 1

HCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate収率 96.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

t-butyl 4-hydroxymethyl-1-piperidinecarboxylate (5.00 g, 23.2 mmol)was dissolved in tetrahydrofuran (75 ml). To the solution were added triethylamine (2.83 g) and methanesulfonyl chloride (3.19 g) under ice cooling, and the mixture was stirred at 0° C. for 5 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate twice. The organic layer was washed with 1N-hydrochloric acid and a saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting solid materials were washed with hexane to give the titled compound (6.55 g, 22.3 mmol, Yield 96%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate twice
  2. washThe organic layer was washed with 1N-hydrochloric acid
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting solid materials were washed with hexane

出典と根拠

ORDレコード
ord-d5af42258f3947f4bd5b4baceed7c4bd
出典データセット
uspto-grants-2008_03
特許番号
US07348324B2

反応ノート

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