Water → HCID 18675812, compound

HRID 1354773Notes

Reaction equation

HRID 1354773 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1.C(OC([N:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1)=O)(C)(C)C.O>C(OCC)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:24]2([OH:27])[CH2:25][CH2:26][NH:21][CH2:22][CH2:23]2)=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 8170982-Bromo-5-chloropyridineHCID 178418339Butyllithium

Product 1

HCID 18675812HCID 18675812, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Butyllithium (15% in hexane; 7.6 ml) was added dropwise to a solution of 2-bromo-5-chloropyridine (2.0 g) in diethyl ether (50 ml) at −78° C. and, after one hour, a solution of N-tert-butoxycarbonyl-4-piperidinone (2.1 g) in diethyl ether (10 ml) was added dropwise. After 30 minutes, water was cautiously added, and the mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was treated by method G. This resulted in the product with the molecular weight of 212.68 (C10H13ClN2O); MS(ESI): 213 (M+H+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe residue was treated by method G
  6. customThis resulted in the product with the molecular weight of 212.68 (C10H13ClN2O)

Sources & evidence

ORD record
ord-87b13609c58a408cb72dcd265a77c57f
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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