Phthalimide → HCID 86699356, compound

HRID 333992Notes

Reaction equation

HRID 333992 reaction equation
[CH2:1]([N:8]([CH2:16][C@@H:17](O)[CH3:18])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]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>O1CCCC1>[CH2:1]([N:8]([CH2:16][C@H:17]([N:24]1[C:20](=[O:30])[C:21]2[C:22](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:23]1=[O:25])[CH3:18])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86699357HCID 86699357, compound

Product 1

HCID 86699356HCID 86699356, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

209 mg of (S)-tert-butyl benzyl(2-hydroxypropyl)carbamate was dissolved in 10 mL of tetrahydrofuran in a nitrogen atmosphere and cooled to 0° C. 173 mg of phthalimide, 413 mg of triphenylphosphine, and 0.31 mL of diisopropyl azodicarboxylate were added thereto, and the mixture was stirred at room temperature for 10 hours. The reaction solution was concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain 278 mg of the title compound as a pale yellow oil (89%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe obtained crude product
  3. customwas purified by silica gel column chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-f8d457acc9cd49a5bb7dd01c36f2da45
Source dataset
uspto-grants-2014_11
Patent number
US08883792B2

Reaction notes

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