Diethyl 4-(benzyloxy)pyridine-2,6-dicarboxylate → HCID 11436507, compound

HRID 870283Notes

Reaction equation

HRID 870283 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15](OCC)=[O:16])[N:12]=[C:11]([C:20](OCC)=[O:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCO.[BH4-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:20][OH:21])[N:12]=[C:13]([CH2:15][OH:16])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 53428285Diethyl 4-(benzyloxy)pyridine-2,6-dicarboxylate

Product 1

HCID 11436507HCID 11436507, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 4311764Sodium borohydrideSolvent

Conditions

Temperature
40 °C

Procedure

Over a solution of 5 (3.8 g, 11 mmol) in anhydrous EtOH, NaBH4 was carefully added (2.61 g, 68 mmol). The resulting solution was stirred at 40° C. for 24 h. then the reaction was quenched with H2O. EtOH was rotovaped down half the total volume, extracted with EtOAc (5×) dried with NaSO4 and the solvent was evaporated to obtain 90% of a white solid as the product.

Workup

  1. customthe reaction was quenched with H2O
  2. extractionextracted with EtOAc (5×)
  3. dry with materialdried with NaSO4
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-57ba58d6a9154b7ba7c41a989bdfd391
Source dataset
uspto-grants-2015_03
Patent number
US08969549B2

Reaction notes

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