Triethylamine → (S)-tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate

HRID 522628

反応式

HRID 522628 の反応式
[OH:1][CH2:2][C@H:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.C(N(CC)CC)C.[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>ClCCl>[CH3:26][S:23]([O:1][CH2:2][C@H:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)(=[O:25])=[O:24]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1512577tert-Butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate

生成物 1

HCID 86673567(S)-tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate収率 98.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of (S)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (3.0 g, 13.8 mmol) and triethylamine (4.2 g, 41.4 mmol) in dichloromethane (80 mL) at 0° C. was dropwise added mesyl chloride (1.9 g, 16.5 mmol). The reaction mixture was stirred at 0° C. for 2 hour, and then diluted with dichloromethane (100 mL). The organic layers were washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and concentrated to afford (S)-tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate as a purple oil (4.0 g, 98%), which was directly used in the next step without further purification. MS (ES+) C11H21NO6S requires: 295, found: 240 [M+H-56]+.

後処理

  1. customat 0° C.
  2. washThe organic layers were washed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-d8089c48fc6c46bfad3a755251fe9aa4
出典データセット
uspto-grants-2016_05
特許番号
US09334263B2

関連ノート

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