Benzyl chloroformate → benzyl 5-nitro-1,3-dihydro-2H-isoindole-2-carboxylate

HRID 604627Notes

Reaction equation

HRID 604627 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7]2)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.[CH2:22]([O:29][C:30](Cl)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:30]([O:29][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:31])[CH2:7]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 64244695-Nitroisoindoline

Product 1

HCID 67057710benzyl 5-nitro-1,3-dihydro-2H-isoindole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-nitroisoindoline (1.16 g, 7.79 mmol) in CH2Cl2 (100 mL), was added diisopropylethylamine (2.7 mL, 15.6 mmol) followed by benzylchloroformate (1.2 mL, 8.56 mmol). The mixture was stirred at room temperature under N2 for 1 h. The reaction mixture was diluted with CH2Cl2 and washed with 1N HCl. The organic layer was dried (Na2SO4), filtered and the solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica gel to provide benzyl 5-nitro-1,3-dihydro-2H-isoindole-2-carboxylate. LCMS calc.=321.1; found=320.8 (M+Na)+. 1H NMR (500 MHz, CDCl3): δ 8.22-8.14 (m, 2H); 7.49-7.37 (m, 6H); 5.27 (s, 2H); 4.89 (s, 2H); 4.87 (s, 2H).

Workup

  1. washwashed with 1N HCl
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-ebfa26d1954c4b878c1f1541a2f7ac38
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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