Water → 4-(5-Chloropyridin-2-yl)-4-hydroxycyclohexanecarboxylic acid ethyl ester

HRID 2043105Notes

Reaction equation

HRID 2043105 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1.[CH2:14]([O:16][C:17]([CH:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1)=[O:18])[CH3:15].O>C(OCC)C>[CH2:14]([O:16][C:17]([CH:19]1[CH2:24][CH2:23][C:22]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=2)([OH:25])[CH2:21][CH2:20]1)=[O:18])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 8170982-Bromo-5-chloropyridineHCID 178418339Butyllithium

Product 1

HCID 684258024-(5-Chloropyridin-2-yl)-4-hydroxycyclohexanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Butyllithium (15% in hexane; 15 ml) was added dropwise to a solution of 2-bromo-5-chloropyridine (3.8 g) in diethyl ether (80 ml) at −78° C. and, after one hour, a solution of 4-oxocyclohexanecarboxylic acid ethyl ester (3.7 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 purified by preparative HPLC. The product with the molecular weight of 283.76 (C14H18ClNO3); MS (ESI): 284 (M+H+) was obtained in this way.

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. customThe residue was purified by preparative HPLC
  6. customMS (ESI): 284 (M+H+) was obtained in this way

Sources & evidence

ORD record
ord-9933fecbf61b4105be515fabf9731120
Source dataset
uspto-grants-2013_11
Patent number
US08586609B2

Reaction notes

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