tert-Butanol → tert-Butyl [2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]carbamate

HRID 1699220Notes

Reaction equation

HRID 1699220 reaction equation
[C:1]1(=[O:16])[N:5]([CH2:6][CH2:7]C(O)=O)[C:4](=[O:11])[C:3]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]12.C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>C1C=CC=CC=1>[C:41]([O:45][C:22]([NH:19][CH2:7][CH2:6][N:5]1[C:1](=[O:16])[C:2]2=[CH:15][CH:14]=[CH:13][CH:12]=[C:3]2[C:4]1=[O:11])=[O:31])([CH3:44])([CH3:43])[CH3:42]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 768593-Phthalimidopropionic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 11483141tert-Butyl [2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]carbamateYield 72.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-(phthalimido)propionic acid (6.0 g) and triethylamine (2.77 g) in benzene (60 ml) was added diphenylphosphoryl azide (7.53 g), and the mixture was refluxed for 40 minutes. Tert-butanol (4.23 g) was added thereto, and the mixture was refluxed overnight. After cooling, the reaction mixture was washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (n-hexane-ethyl acetate) and crystallized from diisopropyl ether to give N-(2-tert-butoxycarbonylaminoethyl)phthalimide (5.74 g) as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed for 40 minutes
  2. temperaturethe mixture was refluxed overnight
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with saturated sodium bicarbonate solution, water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography (n-hexane-ethyl acetate)
  8. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-577451bae8164a3eb3bc6455760e9c29
Source dataset
uspto-grants-2002_02
Patent number
US06344462B1

Reaction notes

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