Phthalimide → HCID 89666941, compound

HRID 2171272Notes

Reaction equation

HRID 2171272 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:45][C:46]1([CH3:61])[CH2:48][CH:47]1[CH:49](O)[C@@H:50]([NH:52][C:53](=[O:59])[O:54][C:55]([CH3:58])([CH3:57])[CH3:56])[CH3:51]>C1COCC1>[CH3:61][C:46]1([CH3:45])[CH2:48][CH:47]1[CH:49]([N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6])[C@@H:50]([NH:52][C:53](=[O:59])[O:54][C:55]([CH3:58])([CH3:57])[CH3:56])[CH3:51]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 89666883HCID 89666883, compound

Product 1

HCID 89666941HCID 89666941, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phthalimide (0.147 g), triphenylphosphine (0.34 g), and diisopropyl azodicarboxylate (0.684 ml) were added to a THF (5 ml) solution containing tert-butyl ((2S)-1-(2,2-dimethylcyclopropyl)-1-hydroxypropan-2-yl)carbamate (0.20 g), followed by stirring at room temperature for 1.5 hours. The solvent was distilled away under reduced pressure and the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:0.2). A yellow liquid of tert-butyl ((2S)-1-(2,2-dimethylcyclopropyl)-1-(1,3-dioxoisoindolin-2-yl)propan-2-yl)carbamate (22.4 mg) was thus obtained.

Workup

  1. distillationThe solvent was distilled away under reduced pressure
  2. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:0.2)

Sources & evidence

ORD record
ord-72be276fc77e4fa78bab6b2b5c67c7db
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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