Hydrogen Peroxide → HCID 10022866, compound

HRID 465619Notes

Reaction equation

HRID 465619 reaction equation
[CH2:1]([C@@H:4]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH:2]=[CH2:3].C1(C2CCCCCCCC2)BCCCCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:50]1[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=1.[OH-].[Na+].OO>O1CCCC1.CCOCC>[N:52]1[CH:53]=[CH:54][CH:55]=[C:50]([CH2:3][CH2:2][CH2:1][C@H:4]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH:51]=1

Participants

9

Reactant 6

HCID 784Hydrogen PeroxideHCID 122863-BromopyridineHCID 14798Sodium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 10402792methyl 4(S)-allyl-8-(benzyloxy)octanoateHCID 178418648HCID 178418648, compound

Product 1

HCID 10022866HCID 10022866, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of methyl 4(S)-allyl-8-(benzyloxy)octanoate (2.4 g, 7.9 mmol) in dry tetrahydrofuran (20 ml) under nitrogen is added a 0.5 M solution of 9-borabicyclononane in tetrahydrofuran (23.6 ml, 11.8 mmol) and the mixture is allowed to stir at room temperature for 18 hours. The reaction mixture is added to a solution of tetrakis-triphenylphosphine palladium (O) (0.13 g, 0.11 mmole as catalyst) and potassium phosphate (5.36 g, 23.3 mmole in tetrahydrofurane (4 ml). Then 3-bromopyridine (1.2 ml, 12.5 mmol) is added and the mixture is heated at reflux for 48 hours. The reaction mixture is cooled down to 0° C. and a 15% solution of sodium hydroxide (8.9 ml) is added followed by hydrogen peroxide (8.9 ml, 30% solution). The mixture is stirred at room temperature for 1.5 hour and then diluted with ether. The organic phase is washed with brine (3×30 ml) and saturated sodium sulfite solution (30 ml). The organic phase is dried, filtered and evaporated to give a dark oil which is purified by flash chromatography on silica gel using 3:2 ether/hexane as eluent to yield methyl 4(R)-[3-(3-pyridyl)propyl]-8-(benzyloxy)octanoate; IR (CH2Cl2): 1732, 1101, 896 cm- 1.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 48 hours
  3. temperatureThe reaction mixture is cooled down to 0° C.
  4. stirringThe mixture is stirred at room temperature for 1.5 hour
  5. washThe organic phase is washed with brine (3×30 ml) and saturated sodium sulfite solution (30 ml)
  6. customThe organic phase is dried
  7. filtrationfiltered
  8. customevaporated
  9. customto give a dark oil which
  10. customis purified by flash chromatography on silica gel using 3:2 ether/hexane as eluent

Sources & evidence

ORD record
ord-4e266ac6a3bd4c498ad6acbf71707418
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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