Phthalimide → HCID 19705467, compound

HRID 727547Notes

Reaction equation

HRID 727547 reaction equation
O[CH2:2][CH2:3][CH:4]([C:12]1([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]1=[O:24])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:60]1(=[O:70])[NH:64][C:63](=[O:65])[C:62]2=[CH:66][CH:67]=[CH:68][CH:69]=[C:61]12>C1COCC1>[O:65]=[C:63]1[C:62]2[C:61](=[CH:69][CH:68]=[CH:67][CH:66]=2)[C:60](=[O:70])[N:64]1[CH2:2][CH2:3][CH:4]([C:12]1([CH2:25][CH:26]([CH3:27])[CH3:28])[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:13]1=[O:24])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 19705520HCID 19705520, compound

Product 1

HCID 19705467HCID 19705467, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl α-(2-hydroxyethyl)-3-(2-methylpropyl)-2-oxo-1-(phenylmethyl)-3-pyrrolidineacetate (435 mg, 1.12 mmol) in dry THF (10 mL) is treated with triphenylphosphine (323 mg, 1.23 mmol), diethylazodicarboxylate (194 μL, 1.23 mmol), and phthalimide (181 mg, 1.23 mmol). The solution is allowed to stir overnight at room temperature under N2. The reaction mixture is concentrated and purified by silica gel chromatography (25 g SG, 20% EtOAc/hexane) to give 518 mg (89%) of the title compound as an off-white, amorphous solid.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompurified by silica gel chromatography (25 g SG, 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-7d2440bacf684c868ded18679ac417c3
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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