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Phthalimide → HCID 71247588, compound

HRID 715068
Notes
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Reaction equation

HRID 715068 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9](O)[C:10]2([F:22])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[F:8].[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:28]2[C:24](=[O:34])[C:25]3[C:26](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:27]2=[O:29])[C:10]2([F:22])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[F:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 71247082HCID 71247082, compound

Product 1

HCID 71247588HCID 71247588, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 77 (194.9 mg, 0.560 mmol) and THF (5.6 mL) cooled to 0° C. was added phthalimide (90.70 mg, 0.616 mmol) and Ph3P (191.1 mg, 0.729 mmol). The reaction mixture was then treated with DEAD (331.8 μL, 0.729 mmol) and warmed to RT and stirred for 16 h. The reaction mixture was concentrated in vacuo. The crude product was purified by SiO2 Biotage chromatography eluting with hexanes/acetone to afford 238.5 mg (89.2%) of tert-butyl 3-((3-chloro-4-fluorophenyl)(1,3-dioxoisoindolin-2-yl)methyl)-3-fluoropyrrolidine-1-carboxylate (79): LC/MS: [M+1-100] m/z 377.0, 379.0.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe crude product was purified by SiO2 Biotage chromatography
  3. washeluting with hexanes/acetone

Sources & evidence

ORD record
ord-d56f52cb9fa242ce811898a7f994deec
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187462B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes