Pyridine → HCID 118114583, compound

HRID 1050582Notes

Reaction equation

HRID 1050582 reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][CH2:4][N:3]1[C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1.[CH:20]1(B(O)O)[CH2:22][CH2:21]1.N1C=CC=CC=1>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH:20]1([N:6]2[CH2:5][CH2:4][N:3]([C@@H:7]3[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]3)[C:2]2=[O:1])[CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 2760897Cyclopropylboronic acidHCID 118114408HCID 118114408, compound

Product 1

HCID 118114583HCID 118114583, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (R)-tert-butyl 3-(2-oxoimidazolidin-1-yl)piperidine-1-carboxylate (365) (10.0 g, 31.17 mmol), cyclopropylboronic acid (6.39 g, 74.35 mmol) and pyridine (8.82 g, 111.5 mmol) in anhydrous DMF (100 mL) was added Cu(OAc)2 (6.75 g, 37.17 mmol). The resulting mixture was stirred at 40° C. under O2 atmosphere (balloon) for 48 hours. After quenched with NH3.H2O (10 mL), the mixture was diluted with water (50 mL) and extracted with EtOAc (100 mL×3). The organic layers were combined, washed with brine, dried, concentrated, and subjected to silica flash column chromatography using 0 to 70% EtOAc in PE to isolate (R)-tert-butyl 3-(3-cyclopropyl-2-oxoimidazolidin-1-yl)piperidine-1-carboxylate (391) (2.6 g, 23%) as a light yellow oil.

Workup

  1. customAfter quenched with NH3.H2O (10 mL)
  2. additionthe mixture was diluted with water (50 mL)
  3. extractionextracted with EtOAc (100 mL×3)
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1b6cf59998dd4efa808e9d1e15e152c3
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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