Phthalimide → HCID 22675315, compound

HRID 1006067Notes

Reaction equation

HRID 1006067 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[O:15]([CH2:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]O)[Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].[C:32]1(=[O:42])[NH:36][C:35](=[O:37])[C:34]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:33]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[O:15]([CH2:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][C:41]1[CH:40]=[CH:39][CH:38]=[C:34]2[C:35]([NH:36][C:32](=[O:42])[C:33]=12)=[O:37])[Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10658493(3-((Tert-butyldimethylsilyloxy)methyl)phenyl)methanol

Product 1

HCID 22675315HCID 22675315, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diisopropyl azodicarboxylate (7.41 g, 36.6 mmol) in THF (23 mL) was added dropwise to a suspension of 3-(tert-butyldimethylsiloxymethyl)-benzyl alcohol (9.25 g, 36.6 mmol), phthalimide (5.39 g, 36.6 mmol) and tripheylphosphine (9.61 g, 36.6 mmol) in THF (50 mL) at room temperature, and the resulting mixture was stirred for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with diethyl ether and stirred at room temperature for 30 minutes. The reaction solution was filtered and the filtrate was concentrated under reduced pressure. The concentration residue was purified by the use of a silica gel column (silica gel 500 mL; hexane−ethyl acetate=10/1−7/1) to obtain the title compound (11.93 g, 85%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with diethyl ether
  3. stirringstirred at room temperature for 30 minutes
  4. filtrationThe reaction solution was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe concentration residue was purified by the use of a silica gel column (silica gel 500 mL; hexane−ethyl acetate=10/1−7/1)

Sources & evidence

ORD record
ord-ade4815b520d4c7881d45fffdd7efb44
Source dataset
uspto-grants-2004_09
Patent number
US06787560B2

Reaction notes

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