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Triethylamine → trans(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-yl methanesulfonate

HRID 43914
ノート
印刷プレビュー

反応式

HRID 43914 の反応式
C(N(CC)CC)C.[C:8]1([CH:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:15]2[CH2:18][C@@H:17]([OH:19])[C@@H:16]2[CH2:20][CH3:21])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl.C(OCC)(=O)C>[CH3:28][S:29]([O:19][C@@H:17]1[CH2:18][N:15]([CH:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:16]1[CH2:20][CH3:21])(=[O:31])=[O:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86648812trans(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-ol

生成物 1

HCID 86648814trans(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-yl methanesulfonate収率 90.9%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回
HCID 8857
Ethyl Acetate
溶媒

実験手順

Triethylamine (0.94 mL, 6.74 mmol) was added to a solution of trans(±)-1-(Diphenylmethyl)-2-ethylazetidin-3-ol obtained in Example (234b) (1.20 g, 4.49 mmol) in dichloromethane (8 mL). Then, a solution of methanesulfonyl chloride (0.45 mL, 5.83 mmol) in dichloromethane (1.5 mL) was added dropwise at room temperature, followed by stirring for four hours. The reaction solution was diluted with ethyl acetate, washed with water and brine, and then dried over anhydrous magnesium sulfate. Following filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1) to obtain 1.41 g of the title compound as a pale yellow oily substance (91%).

後処理

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-0a3c6780d25c413b89cc03f2fcab2449
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08536197B2

反応ノート

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