Diethyl Ether → HCID 71738666, compound

HRID 1752843Notes

Reaction equation

HRID 1752843 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[CH2:6][CH2:7][CH:8]=O)([O-])=O.CCCN1[C@@H]2CCC3C=CC(O)=CC=3[C@H]2[O:20]CC1.C(OCC)C>CS(C)=O.N1CCC[C@H]1C(O)=O.CO.[Pd]>[NH:1]1[C:4]2[C:5](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:6][C@@H:7]([OH:20])[CH2:8]1

Participants

8

Reactant 3

HCID 3283Diethyl EtherHCID 57533NaxagolideHCID 105592503-(2-Nitrophenyl)propanal

Product 1

HCID 71738666HCID 71738666, compound

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 23938PalladiumSolventHCID 145742L-ProlineSolvent

Procedure

To a stirred solution of o-nitrohydrocinnamaldehyde 4a-e (6 mmol) and PhNO (6 mmol) in DMSO (20 mL), L-proline (20 mol %) was added at 25° C. and allowed to stir for 20 min. After completion of reaction, as indicated by the change in color from green to yellow, large excess (100 mL) of diethyl ether was poured into the reaction mixture and stirred for additional 10 min. The combined organic mixture was washed with H2O (5×20 mL). The organic layer was separated and aqueous layer was extracted with diethyl ether (2×50 mL). Combined organic layers were washed with brine (5×50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude product. The crude α-aminooxylated aldehyde was dissolved in MeOH (20 mL) and to this mixture 10% Pd/C (5 wt %) was added. The reaction mixture was then stirred at 25° C. for additional 6 h. After the completion of reaction (monitored by TLC), it was filtered through celite and the solvent evaporated under reduced pressure. Chromatographic purification of the crude product [flash silica gel (230-400 mesh) and pet. ether:EtOAc:Et3N (60:38:2)] gave the pure (R)-tetrahydroquinolin-3-ol derivatives 5a-e.

Workup

  1. customAfter completion of reaction
  2. additionwas poured into the reaction mixture
  3. stirringstirred for additional 10 min
  4. washThe combined organic mixture was washed with H2O (5×20 mL)
  5. customThe organic layer was separated
  6. extractionaqueous layer was extracted with diethyl ether (2×50 mL)
  7. washCombined organic layers were washed with brine (5×50 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customto give the crude product
  11. additionwas added
  12. stirringThe reaction mixture was then stirred at 25° C. for additional 6 h
  13. customAfter the completion of reaction (monitored by TLC), it
  14. filtrationwas filtered through celite
  15. customthe solvent evaporated under reduced pressure
  16. customChromatographic purification of the crude product [flash silica gel (230-400 mesh) and pet. ether:EtOAc:Et3N (60:38:2)]

Sources & evidence

ORD record
ord-5a27ee7e8fe34beaaae8a4301d7f5238
Source dataset
uspto-grants-2015_10
Patent number
US09163038B2

Reaction notes

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