Diethyl Ether → HCID 131716321, compound

HRID 1199736Notes

Reaction equation

HRID 1199736 reaction equation
[ClH:1].[OH:2][C@@H:3]1[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:8][C:7]2[C:18]([C:22]([F:25])([F:24])[F:23])=[CH:19][CH:20]=[CH:21][C:6]=2[N:5]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[C:4]1=[O:33].[H][H].CCOCC>C(O)C.CC#N.C(O)(C)C.O=[Pt]=O>[ClH:1].[OH:2][C@@H:3]1[C@H:9]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[CH2:8][C:7]2[C:18]([C:22]([F:23])([F:25])[F:24])=[CH:19][CH:20]=[CH:21][C:6]=2[N:5]([CH2:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][NH:28]2)[C:4]1=[O:33]

Participants

8

Reactant 3

HCID 3283Diethyl EtherHCID 14821846HCID 14821846, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131716321HCID 131716321, compound

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 3.00 g (6.09 mmol) of the title compound from Example 23 in 200 ml of ethanol was treated with 0.30 g of PtO2 and placed on the Parr apparatus under 50 psi of hydrogen for 2 hours. TLC at this point indicated the reduction of the pyridyl group was complete. The catalyst was filtered under nitrogen and solvent evaporated to give a solid residue. The latter was dissolved in 30 ml of CH3CN and luted with 330 ml of ether to give a solid. This mixture was cooled overnight and filtered to give 1.29 g (43%) of Isomer A, m.p. 177°-180° C. (s. 160° C.). Isomer A was dissolved in 20 ml of hot isopropyl alcohol, filtered through filter cel (to remove trace of catalyst), cooled overnight and filtered to give 0.72 g of nearly colorless solid, [α]D +112°, (c=1.0 MeOH). After recrystallization from 18 ml of hot isopropyl alcohol, the product weighed 0.63 g (21%); m.p. 177°-180° C. (s. 160° C.); [α]D +113° C. (c=1.0, MeOH); Rf 0.59 (80:20 CH2Cl2 -MeOH).

Workup

  1. filtrationThe catalyst was filtered under nitrogen
  2. customsolvent evaporated
  3. customto give a solid residue
  4. customto give a solid
  5. temperatureThis mixture was cooled overnight
  6. filtrationfiltered
  7. customto give 1.29 g (43%) of Isomer A, m.p. 177°-180° C. (s. 160° C.)
  8. filtrationfiltered
  9. filtrationthrough filter
  10. customcel (to remove trace of catalyst)
  11. temperaturecooled overnight
  12. filtrationfiltered
  13. customto give 0.72 g of nearly colorless solid, [α]D +112°, (c=1.0 MeOH)
  14. customAfter recrystallization from 18 ml of hot isopropyl alcohol
  15. customm.p. 177°-180° C. (s. 160° C.)

Sources & evidence

ORD record
ord-96dbdbe7606942a2a2f3dd67dca65ecf
Source dataset
uspto-grants-1990_02
Patent number
US04902684

Reaction notes

Loading…