홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Dimethyl Sulfoxide → tert-butyl 5-oxo-octahydro-1H-isoindole-2-carboxylate

HRID 1059314
노트
인쇄 미리보기

반응식

HRID 1059314 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:26][CH:25]2[CH:20]([CH2:21][CH2:22][CH:23]([OH:27])[CH2:24]2)[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:26][CH:25]2[CH:20]([CH2:21][CH2:22][C:23](=[O:27])[CH2:24]2)[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 186703241,1-Dimethylethyl octahydro-5-hydroxy-2H-isoindole-2-carboxylate

생성물 1

HCID 18670457tert-butyl 5-oxo-octahydro-1H-isoindole-2-carboxylate수율 86.8%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
4회

반응 조건

온도
-78 °C

실험 절차

4.9 g of oxalyl chloride was dissolved in 250 ml of dichloromethane and cooled to −78° C. in a nitrogen atmosphere. Then a solution of 4.83 g of dimethyl sulfoxide in dichloromethane (20 ml) was dropped thereinto over 17 minutes. Subsequently, a solution of 3.73 g of 8-(tert-butoxycarbonyl)-8-azabicyclo[4.3.0]nonan-3-ol in dichloromethane (40 ml) was dropped thereinto over 10 minutes. After stirring for 10 minutes, 7.82 g of triethylamine was dropped thereinto over 10 minutes and stirring was continued for additional 1 hour. The reaction mixture was brought back to room temperature, diluted with dichloromethane, washed with water and a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 3.21 g of the title compound as a colorless oily substance.

후처리

  1. waitover 10 minutes
  2. waitover 10 minutes
  3. stirringstirring
  4. waitwas continued for additional 1 hour
  5. customwas brought back to room temperature
  6. washwashed with water
  7. dry with materiala saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-4a5ed146f509423cb0807849304716f4
출처 데이터셋
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06518423B1

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트