Ethanol → Tert-butyl (1,3-dioxoisoindolin-2-yl)(ethyl)carbamate

HRID 220391

반응식

HRID 220391 반응식
N(C(OC(C)C)=O)=NC(O[CH:6](C)[CH3:7])=O.[O:15]=[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=[O:25])[N:17]1[NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>C1COCC1>[O:25]=[C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16](=[O:15])[N:17]1[N:26]([CH2:6][CH3:7])[C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31]

참가 물질

6

반응물 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 801162N-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)(tert-butoxy)formamide

생성물 1

HCID 58180562Tert-butyl (1,3-dioxoisoindolin-2-yl)(ethyl)carbamate수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Diisopropyl azodicarboxylate (2.92 mL, 15.00 mmol) was added in one portion to a solution of tert-butyl 1,3-dioxoisoindolin-2-ylcarbamate (2.62 g, 10 mmol, prepared following the procedure described by Nicolas Brosse et al. in Eur. J. Org. Chem. 4757-4764, 2003), triphenylphosphine (3.93 g, 15.00 mmol) and ethanol (0.691 g, 15.00 mmol) in THF (20 mL) at 0° C. and the reaction solution was stirred at room temperature for 1 h (monitored by TLC until completion). Solvent was evaporated and the residue was purified by flash chromatography on silica gel using an automated ISCO system (80 g column, eluting with 5-35% ethyl acetate/hexanes) to provide tert-butyl 1,3-dioxoisoindolin-2-yl(ethyl)carbamate (2.6 g, 90% yield) as a white solid which was used as it in the next step

후처리

  1. customprepared
  2. customSolvent was evaporated
  3. customthe residue was purified by flash chromatography on silica gel using
  4. washan automated ISCO system (80 g column, eluting with 5-35% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-b6370719cb7e4c7da45ef65d63ea9453
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202881B2

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