tert-Butyl 4-methoxy-4-(2-diazo-1,3-dioxopent-1-yl)piperidine-1-carboxylate → tert-Butyl 4-oxo-3-(1-oxoprop-1-yl)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

HRID 8759

반응식

HRID 8759 반응식
[CH3:1][O:2][C:3]1([C:16](=[O:24])[C:17](=[N+]=[N-])[C:18](=[O:21])[CH2:19][CH3:20])[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>ClCCl.Cl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[O:24]=[C:16]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[O:2][CH2:1][CH:17]1[C:18](=[O:21])[CH2:19][CH3:20]

참가 물질

5

반응물 1

HCID 73857865tert-Butyl 4-methoxy-4-(2-diazo-1,3-dioxopent-1-yl)piperidine-1-carboxylate

생성물 1

HCID 21983892tert-Butyl 4-oxo-3-(1-oxoprop-1-yl)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate수율 40.4%

시약·촉매·용매 3

HCID 152122Dirhodium tetraacetate촉매HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매2회

실험 절차

A solution of rhodium acetate dimer (0.002 g, 0.005 mmol) in dichloromethane (27 mL) was heated to 81° C. A solution of tert-butyl 4-methoxy-4-(2-diazo-1,3-dioxopent-1-yl)piperidine-1-carboxylate (0.092 g, 0.270 mmol) from Step D in dichloromethane (7 mL) was added slowly dropwise over 12 min. The reaction mixture was refluxed for 45 min then poured into IN hydrochloric acid, and extracted three times with dichloromethane. The organic layers were combined, washed with saturated sodium chloride solution, dried over sodium sulfite, filtered, and concentrated. The residue was purified by flash chromatography eluting with 10% ethyl acetate/dichloromethane to afford the title compound (0.034 g).

후처리

  1. temperatureThe reaction mixture was refluxed for 45 min
  2. extractionextracted three times with dichloromethane
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfite
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 10% ethyl acetate/dichloromethane

출처 및 근거

ORD 기록
ord-877888e2a7554dd4b0bc69673d1bcb3a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091211B2

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