Phthalimide → tert-Butyl alpha-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate

HRID 727529Notes

Reaction equation

HRID 727529 reaction equation
N(C(OCC)=O)=NC(OCC)=O.O[CH2:14][CH2:15][CH:16]([C:24]1([CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]1=[O:37])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:61]1(=[O:71])[NH:65][C:64](=[O:66])[C:63]2=[CH:67][CH:68]=[CH:69][CH:70]=[C:62]12>C1COCC1>[O:66]=[C:64]1[C:63]2[C:62](=[CH:70][CH:69]=[CH:68][CH:67]=2)[C:61](=[O:71])[N:65]1[CH2:14][CH2:15][CH:16]([C:24]1([CH2:38][CH:39]([CH3:40])[CH3:41])[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:25]1=[O:37])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19705471tert-Butyl alpha-(2-Hydroxyethyl)-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate

Product 1

HCID 19705454tert-Butyl alpha-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetateYield 52.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (182 uL, 1.16 mmol) is added to a mixture of tert-butyl α-(2-hydroxyethyl)-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (468 mg, 1.16 mmol), triphenylphosphine (304 mg, 1.16 mmol), phthalimide (171 mg, 1.16 mmol) and THF (10 mL) at room temperature. The mixture is allowed to stir overnight and is concentrated. Purification by column chromatography (2 columns, 5% acetone/CH2Cl2 and 10% EtOAc/hexane) provided 327 mg (51%) of the title compound as a colorless oil.

Workup

  1. concentrationis concentrated
  2. customPurification by column chromatography (2 columns, 5% acetone/CH2Cl2 and 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-6c80a661624f456783ef7b34b65d528f
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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