Di-tert-butyl dicarbonate → tert-Butyl 5-iodoisoindoline-2-carboxylate

HRID 710466Notes

Reaction equation

HRID 710466 reaction equation
FC(F)(F)C(O)=O.[I:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][NH:13][CH2:12]2.[O:18](C(OC(C)(C)C)=O)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=O>N1C=CC=CC=1>[I:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[CH2:12]2

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 66726889HCID 66726889, compound

Product 1

HCID 57753580tert-Butyl 5-iodoisoindoline-2-carboxylateYield 78.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of the product of Step A (0.77 g; 2.15 mmol) and (BOC)2O (0.7 g; 3.2 mmol) in anhydrous pyridine (3 ml) was stirred for 1 h at ˜70° C. After removing solvents under reduced pressure, the residue was diluted to 20 ml with Et2O. The insoluble material was filtered off, and filtrate was washed with diluted HCl (5 ml), saturated NaHCO3 (5 ml), brine and dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; CH2Cl2:hexane 1:1) to give title compound (0.58 g; 78%) as creamy oil. 1H-NMR (CDCl3) 1.49 (5, 9H); 4.58-4.63 (m, 4H); 6.9-7.04 (m, 1H); 7.5-7.63 (m, 2H).

Workup

  1. customAfter removing solvents under reduced pressure
  2. additionthe residue was diluted to 20 ml with Et2O
  3. filtrationThe insoluble material was filtered off
  4. washfiltrate was washed with diluted HCl (5 ml), saturated NaHCO3 (5 ml), brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customthe residue was purified by FCC (SiO2; CH2Cl2:hexane 1:1)

Sources & evidence

ORD record
ord-4b186fc5e275486da349c2b2cb5f6a53
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

Loading…