Phthalimide → HCID 58833975, compound

HRID 1672751Notes

Reaction equation

HRID 1672751 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13]O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][N:19]1[C:15](=[O:25])[C:16]2[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:18]1=[O:20])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 58833975HCID 58833975, compoundYield 114.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Commercially available (S)-(−)-1-tert-butoxycarbonyl-2-pyrrolidinemethanol (1.00 g, 4.97 mmol) was dissolved in toluene (10 mL), and the mixture was stirred at room temperature for 1.5 hours after adding phthalimide (877 mg, 5.96 mmol), triphenylphosphine (1.96 g, 7.46 mmol), and diethyl azodicarboxylate (40% toluene solution, 3.4 mL, 7.46 mmol). The mixture was further stirred at 60° C. for 4 hours. Thereafter, water and ethyl acetate were added to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give (S)-2-[(1,3-dioxoisoindolin-2-yl)methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.88 g, quantitative).

Workup

  1. stirringThe mixture was further stirred at 60° C. for 4 hours
  2. customto separate the organic layer
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-779dbc63c36e41b787e1f855d1af7bc5
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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