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

HRID 70784

반응식

HRID 70784 반응식
[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

참가 물질

7

반응물 4

HCID 679Dimethyl Sulfoxide2회HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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),

후처리

  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)

출처 및 근거

ORD 기록
ord-7a1082cecff047baad1b5aa5230fb810
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822688B2

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