Methyl chloroformate → 5-(Methoxycarbonylamino)isoindoline.hydrochloride

HRID 22961Notes

Reaction equation

HRID 22961 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]([O:11][CH3:12])=[O:10].[NH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2.Cl.O1CCOCC1>O1CCOCC1.O.C(Cl)Cl>[ClH:8].[CH3:12][O:11][C:9]([NH:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[CH2:19][NH:18][CH2:17]2)=[O:10]

Participants

8

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 204431481,4-Dioxane hydrochlorideHCID 22591361tert-butyl 5-amino-2,3-dihydro-1H-isoindole-2-carboxylate

Product 1

HCID 225913645-(Methoxycarbonylamino)isoindoline.hydrochloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

0.85 ml of triethylamine and 0.35 ml of methyl chloroformate were added to 8 ml of a methylene chloride solution containing 0.72 g of 5-amino-2-tert-butoxycarbonylisoindoline, and the mixture was stirred at room temperature for 5 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. After the extract was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (solvent: chloroform-ethyl acetate=2:1) to obtain an oil. This oil was dissolved in 5 ml of dioxane, then, 8 ml of 4N hydrochloric acid-dioxane was added thereto, and the mixture was stirred at room temperature. The precipitates precipitated by addition of 20 ml of ether were collected by filtration and washed with ether to obtain 5-(methoxycarbonylamino)isoindoline.hydrochloride.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialAfter the extract was dried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel chromatography (solvent: chloroform-ethyl acetate=2:1)
  5. customto obtain an oil
  6. stirringthe mixture was stirred at room temperature
  7. customThe precipitates precipitated by addition of 20 ml of ether
  8. filtrationwere collected by filtration
  9. washwashed with ether

Sources & evidence

ORD record
ord-cf0c30d0d12648b4a2f0e76d5674e203
Source dataset
uspto-grants-2005_02
Patent number
US06849622B2

Reaction notes

Loading…