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

HRID 1188069Notes

Reaction equation

HRID 1188069 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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

Workup

  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)

Sources & evidence

ORD record
ord-3606999523cf463d8230850592afeced
Source dataset
uspto-grants-2014_03
Patent number
US08673933B2

Reaction notes

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