Phthalimide → HCID 22633658, compound

HRID 2416995Notes

Reaction equation

HRID 2416995 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]1[CH:21]2[CH:16]([CH:17]3[CH2:22][CH:20]2[CH2:19][CH:18]3O)[CH2:15][CH2:14]1.[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:13]1[CH:21]2[CH:16]([CH:17]3[CH2:22][CH:20]2[CH2:19][CH:18]3[N:28]2[C:24](=[O:34])[C:25]3[C:26](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:27]2=[O:29])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 95606Octahydro-4,7-methano-1H-inden-5-olHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 22633658HCID 22633658, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

With stirring, 1.7 g of diethyl azodicarboxylate, diluted with 5 ml of THF, were added to a solution of 1.66 g of octahydro-4,7-methanoinden-5-ol, 1.47 g of phthalimide, and 2.62 g of triphenylphosphine in 15 ml of THF. The reaction mixture was allowed to stand overnight and then concentrated, the residue was stirred with ether, the precipitate was filtered off with suction, and the filtrate was concentrated. The residue was purified over silica gel using toluene. This gave 1.36 g of a yellow oil.

Workup

  1. concentrationconcentrated
  2. stirringthe residue was stirred with ether
  3. filtrationthe precipitate was filtered off with suction
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified over silica gel

Sources & evidence

ORD record
ord-8ebf88643baa4eb68a7c395c8f033418
Source dataset
uspto-grants-2004_11
Patent number
US06825231B2

Reaction notes

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