1-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid → Tert-butyl 2-(6-phenylpyrimidin-4-yl)pyrrolidine-1-carboxylate

HRID 1394986

Reaction equation

HRID 1394986 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)ncn1

Participants

8

Reactant 2

HCID 2684721-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 5934294-Chloro-6-phenylpyrimidine

Product 1

HCID 118426415Tert-butyl 2-(6-phenylpyrimidin-4-yl)pyrrolidine-1-carboxylateYield 65%

Reagents, catalysts & solvents 5

HCID 10796Cesium carbonateReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylCatalystHCID 15773433Dichloronickel;1,2-dimethoxyethaneCatalystHCID 178441129HCID 178441129, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

Prior to irradiation, the reaction mixture was degassed by bubbling argon for 20 minutes

Workup

  1. additiondiluted with saturated aqueous NaHCO3
  2. additionNo procedure recorded
  3. additionNo procedure recorded
  4. additionNo procedure recorded
  5. extractionextracted with Et2O (3 x 100 mL) · Keep organic
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. 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

Linked notes

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