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Phthalimide → [R]-2-[1-(Phenylmethyl)-3-pyrrolidinyl]-1H-isoindole-1,3(2H)-dione

HRID 232049
Notes
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Reaction equation

HRID 232049 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][C@H:10](O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][C@@H:10]([N:18]3[C:14](=[O:24])[C:15]4[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:17]3=[O:19])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733875(S)-(-)-1-Benzyl-3-pyrrolidinol

Product 1

HCID 14555490[R]-2-[1-(Phenylmethyl)-3-pyrrolidinyl]-1H-isoindole-1,3(2H)-dioneYield 79%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a suspension of 8.9 g (50 mmol) of (S)-1-phenylmethyl-3-hydroxypyrrolidine [Synth. Commun., 15, 587 (1985)], 9.8 g (50 mmol) of phthalimide, 13.1 g (50 mmol) of triphenylphosphine and 100 ml of tetrahydrofuran was added, dropwise, a solution of 8.8 g (50 mmol) of diethyl azodicarboxylate at room temperature. The reaction was stirred for 18 hours and the solvent was removed in vacuo. The residue was triturated with ether and the solid was removed by filtration and chromatographed on silica gel (E. Merck-240-400 mesh) eluting with chloroform/ethyl acetate (80:20). Fractions were combined based on thin layer chromatography and evaporated in vacuo to give 12.1 g of the title compound.

Workup

  1. additionwas added
  2. customat room temperature
  3. customthe solvent was removed in vacuo
  4. customThe residue was triturated with ether
  5. customthe solid was removed by filtration
  6. customchromatographed on silica gel (E. Merck-240-400 mesh)
  7. washeluting with chloroform/ethyl acetate (80:20)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-5247e0e7fe19404ea815cf491954b638
Source dataset
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04851418

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes