4-Pyridinecarboxaldehyde → HCID 57571261, compound

HRID 1423896Notes

Reaction equation

HRID 1423896 reaction equation
[C:1]1([C@H:7]2[NH:12][CH2:11][C:10](=[O:13])[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:14]1[CH:19]=[CH:18][C:17]([CH:20]=[O:21])=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[C:1]1([C@@H:7]2[CH2:8][O:9][C:10](=[O:13])[C@H:11]3[C@H:20]([C:17]4[CH:18]=[CH:19][N:14]=[CH:15][CH:16]=4)[O:21][C@H:20]([C:17]4[CH:18]=[CH:19][N:14]=[CH:15][CH:16]=4)[N:12]23)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 133894-PyridinecarboxaldehydeHCID 11126817(R)-5-phenylmorpholin-2-one

Product 1

HCID 57571261HCID 57571261, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (R)-5-phenylmorpholinon-2-one EBE 06134 (3.0 g, 16.9 mmol) and pyridine-4-carboxaldehyde (5.43 g, 50.7 mmol) in toluene (75 mL) was refluxed in a soxhlet extractor filled with molecular sieves 4A (25 g) for 16 hours. All the volatiles were evaporated and the desired product was purified by column chromatography (SiO2) using a gradient of 80% to 100% [v/v] EtOAc in cyclohexane to give after evaporation (1S,3R,5R,8aR)-tetrahydro-5-phenyl-1,3-di(pyridin-4-yl)oxazolo[4,3-c][1,4]oxazin-8(311)-one EBE 06136 (1.7 g, 46% yield) as a pale yellow solid.

Workup

  1. customAll the volatiles were evaporated
  2. customthe desired product was purified by column chromatography (SiO2)
  3. customto give

Sources & evidence

ORD record
ord-d81a157c436a4553aeec977ada4e789a
Source dataset
uspto-grants-2015_01
Patent number
US08927589B2

Reaction notes

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