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

HRID 613653Notes

Reaction equation

HRID 613653 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-d3a10745d45f493eb7444858837e16f1
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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