1-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid → Tert-butyl 2-(6-phenylpyrimidin-4-yl)pyrrolidine-1-carboxylate
Reaction equation
CC(C)(C)OC(=O)N1CCCC1C(=O)O.Clc1cc(-c2ccccc2)ncn1>CC(C)(C)c1cc[n]2->[Ir+]34([c]5cc(F)cc(F)c5-c5ccc(C(F)(F)F)c[n]->35)([c]3cc(F)cc(F)c3-c3ccc(C(F)(F)F)c[n]->43)<-[n]3ccc(C(C)(C)C)cc3-c2c1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CN(C)C=O.COCCOC.F[P-](F)(F)(F)(F)F.O=C([O-])[O-].[Cl][Ni][Cl].[Cs+].[Cs+]>CC(C)(C)OC(=O)N1CCCC1c1cc(-c2ccccc2)ncn1Participants
8
Reactant 2
Product 1
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 23 °C
Procedure
Prior to irradiation, the reaction mixture was degassed by bubbling argon for 20 minutes
Workup
- additiondiluted with saturated aqueous NaHCO3
- additionNo procedure recorded
- additionNo procedure recorded
- additionNo procedure recorded
- extractionextracted with Et2O (3 x 100 mL) · Keep organic
- washwashed with water and brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- flash chromatographyFluka, 230-400 mesh, solvent system: 20% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-980f59be0fef4944a93d6d926e7c186a
- Source dataset
- Coupling of α-carboxyl sp3-carbons with aryl halides
- Original link
- View source
Reaction notes
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