Dimethyl Sulfoxide → tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HRID 70784

反応式

HRID 70784 の反応式
[H-].[Na+].CS(C)=O.[I-].[CH3:8][S+](C)(C)=O.[O:13]=[C:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1>CCOC(C)=O.O>[O:13]1[C:14]2([CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]2)[CH2:8]1

参加物

7

反応物 4

HCID 679Dimethyl Sulfoxide2 回HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

生成物 1

HCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate収率 80.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

55% sodium hydride (6.02 g) was added under ice-cooling to a DMSO (250 mL) suspension of trimethylsulfoxonium iodide (33.1 g), and stirring was performed at room temperature for 1 hour. A DMSO (125 ml) solution of tert-butyl 4-oxopiperidine-1-carboxylate (25.0 g) was added, and heated and stirred at 60° C. for 1 hour. Purified water was added to the mixture, and extraction was performed with EtOAc. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/hexane) to obtain tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (21.5 g),

後処理

  1. temperatureheated
  2. stirringstirred at 60° C. for 1 hour
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

出典と根拠

ORDレコード
ord-7a1082cecff047baad1b5aa5230fb810
出典データセット
uspto-grants-2014_09
特許番号
US08822688B2

関連ノート

読み込み中…