Ammonium formate → HCID 86749589, compound

HRID 1733901Notes

Reaction equation

HRID 1733901 reaction equation
C([N:8]1[CH2:17][CH2:16][C@H:15]2[C@H:10]([CH2:11][CH2:12][C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)([OH:18])[CH2:14]2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:13]2([OH:18])[CH2:12][CH2:11][C@H:10]3[C@H:15]([CH2:16][CH2:17][NH:8][CH2:9]3)[CH2:14]2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 2723923Ammonium formateHCID 86749590HCID 86749590, compound

Product 1

HCID 86749589HCID 86749589, compound

Procedure

Part A: Nitrogen gas was bubbled through methanol (25 mL). The following reagents were added in order: 10% palladium on carbon (0.5 g), the product of Example 8 (0.5 g, 1.5 mmol) and ammonium formate (1.0 g). The reaction mixture was heated to reflux temperature and stirred for 30 min. The reaction mixture was cooled to ambient temperature and filtered through Celite. The filter pad was washed with methanol and chloroform. The combined filtrates were concentrated in vacuo. The residue was treated with a 1N NaOH solution and extracted three times with ethylacetate. The combined organic layers were dried over magnesium sulfate and filtered. Solvent was removed in vacuo to give cis-6-(4'-fluorophenyl)-6-hydroxydecahydroisoquinoline: NMR (CDCl3, 300 MHz): 7.45 (dd, 2H, J=8, 6), 7.0 (t, 2H, J=8), 3.15-1.4 (m, 16H); HRMS: Calcd: 249. 1529 Found: 249.1531.

Workup

  1. customPart A: Nitrogen gas was bubbled through methanol (25 mL)
  2. additionThe following reagents were added in order
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux temperature
  5. filtrationfiltered through Celite
  6. washThe filter pad was washed with methanol and chloroform
  7. concentrationThe combined filtrates were concentrated in vacuo
  8. additionThe residue was treated with a 1N NaOH solution
  9. extractionextracted three times with ethylacetate
  10. dry with materialThe combined organic layers were dried over magnesium sulfate
  11. filtrationfiltered
  12. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-f832a386d82843ac9d3dfd89e85a3ffe
Source dataset
uspto-grants-1996_07
Patent number
US05532243

Reaction notes

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