Triacetoxyperiodinane → HCID 59178537, compound

HRID 1691747Notes

Reaction equation

HRID 1691747 reaction equation
[F:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][C@@H:15]([CH2:18]O)[C@H:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:13]2)=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].CC(OI1(OC(C)=O)(OC(C)=O)O[C:37](=O)[C:36]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]1=2)=O>ClCCl>[F:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][NH:4][C@@H:3]([C:32]3[C:31]4[C:36](=[CH:37][CH:5]=[CH:6][CH:7]=4)[CH:35]=[CH:34][CH:33]=3)[CH3:2])[CH:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:13]2)=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66905663HCID 66905663, compound

Product 1

HCID 59178537HCID 59178537, compoundYield 154.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 282 mg of methyl rel-5-fluoro-6-[(3R,4R)-4-(hydroxymethyl)-3-phenylpiperidin-1-yl]nicotinate in 3.0 mL of dichloromethane was added 382 mg of Dess-Martin Periodinane at room temperature, followed by stirring for 1.5 hours. This reaction mixture was washed with 1,2-dichloroethane, transferred to a dropping funnel, and added dropwise to a mixture of 147 mg of (1R)-1-(1-naphthyl)ethaneamine, 521 mg of sodium triacetoxyborohydride, 49 mg of acetic acid, and 10 mL of 1,2-dichloroethane at room temperature. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by vigorously stirring for 10 minutes, and then extraction with chloroform. The organic layer was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by NH silica gel (FUJI SILISIA CHEMICAL. Ltd., Japan) column chromatography (hexane-ethyl acetate) to obtain 314 mg of methyl 5-fluoro-6-[4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]nicotinate as a colorless foamy substance.

Workup

  1. washThis reaction mixture was washed with 1,2-dichloroethane
  2. customtransferred to a dropping funnel
  3. additionadded dropwise to a mixture of 147 mg of (1R)-1-(1-naphthyl)ethaneamine, 521 mg of sodium triacetoxyborohydride, 49 mg of acetic acid, and 10 mL of 1,2-dichloroethane at room temperature
  4. additionTo the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution
  5. stirringby vigorously stirring for 10 minutes
  6. extractionextraction with chloroform
  7. washThe organic layer was washed with water and saturated brine in this order
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customthe residue was purified by NH silica gel (FUJI SILISIA CHEMICAL. Ltd., Japan) column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-373dbd14378647ea88cfb40182f76088
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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