Hydrochloric Acid → HCID 86586734, compound

HRID 2088190Notes

Reaction equation

HRID 2088190 reaction equation
[C:1]([NH:4][C@@H:5]1[CH2:11][C@:10]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:12](CC3C=CC=CC=3)[C@H:6]1[CH2:7][CH2:8][C@H:9]2[O:26][CH2:27][C:28]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[C:30]([C:38]([F:41])([F:40])[F:39])[CH:29]=1)(=[O:3])[CH3:2].[ClH:42]>CO.C(OCC)C.[OH-].[Pd+2].[OH-]>[ClH:42].[C:1]([NH:4][C@@H:5]1[CH2:11][C@:10]2([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:12][C@H:6]1[CH2:7][CH2:8][C@H:9]2[O:26][CH2:27][C:28]1[CH:29]=[C:30]([C:38]([F:39])([F:40])[F:41])[CH:31]=[C:32]([C:34]([F:36])([F:35])[F:37])[CH:33]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86586725HCID 86586725, compound

Product 1

HCID 86586734HCID 86586734, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

(1R*,2R*,5S*,6R*)-6-Acetamido-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane (Example 118; 66 mg, 0.11 mmol) was dissolved in methanol (5 ml) and 2N hydrochloric acid (1 ml) and 10% palladium hydroxide (20 mg) added. The reaction mixture was hydrogenated at 40 psi for 1 hour. The mixture was then filtered and concentrated in vacuo then the oil basified (saturated sodium hydrogen carbonate solution) and extracted with dichloromethane (×3), dried (MgSO4) and concentrated in vacuo to give a clear oil. The oil was purified by thin layer chromatography [10% methanol in dichloromethane] to give a white solid. The hydrochloride salt was made by adding 1 equivalent of hydrogen chloride in diethyl ether (1.0M) to a solution in diethyl ether and the title compound-filtered and dried in vacuo at 60° C.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. extractionextracted with dichloromethane (×3)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a clear oil
  7. customThe oil was purified by thin layer chromatography [10% methanol in dichloromethane]
  8. customto give a white solid
  9. filtrationthe title compound-filtered
  10. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-9d7d007afc3e4d44841031602e8640ed
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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