1-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid → tert-Butyl 2-(2-methylpyridin-4-yl)pyrrolidine-1-carboxylate

HRID 1394981Notes

Reaction equation

HRID 1394981 reaction equation
CC(C)(C)OC(=O)N1CCCC1C(=O)O.Cc1cc(Br)ccn1>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+]>Cc1cc(C2CCCN2C(=O)OC(C)(C)C)ccn1

Participants

8

Reactant 2

HCID 2684721-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 27628354-Bromo-2-methylpyridine

Product 1

HCID 102543294tert-Butyl 2-(2-methylpyridin-4-yl)pyrrolidine-1-carboxylateYield 85%

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: 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-cbcfac768325414ab1d753c079ee3782
Source dataset
Coupling of α-carboxyl sp3-carbons with aryl halides
Original link
View source

Reaction notes

Loading…