Triethylamine → HCID 178462273, compound

HRID 2088227Notes

Reaction equation

HRID 2088227 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@:14]([F:27])([C:16]3[N:20](COCCOC)[N:19]=[N:18][N:17]=3)[CH2:15][C@@:9]1([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C@H:10]([O:28][C@H:29]([C:32]1[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[C:34]([C:42]([F:45])([F:44])[F:43])[CH:33]=1)[CH2:30]I)[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>[Pd].CO.C(OCC)(=O)C>[CH2:1]([N:8]1[C@@H:13]2[C@:14]([F:27])([C:16]3[NH:20][N:19]=[N:18][N:17]=3)[CH2:15][C@@:9]1([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C@H:10]([O:28][C@H:29]([C:32]1[CH:33]=[C:34]([C:42]([F:43])([F:44])[F:45])[CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH3:30])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 86586780HCID 86586780, compound

Product 1

HCID 178462273HCID 178462273, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on charcoal (60 mg) was added to a solution of (1R*,2R*,5S*,6S*)-8-benzyl-2-{(1R*)-1-[3,5-bis(trifluoromethyl)phenyl]-2-iodoethoxy}-6-fluoro-6-[1-(2-methoxyethoxymethyl)-1H-tetrazol-5-yl]-1-phenyl-8-azabicyclo[3.2.1]octane (Description 46; 193 mg, 0.23 mmol) and triethylamine (38 mg, 0.38 mmol) in methanol (3 ml) and ethyl acetate (5 ml). The mixture was hydrogenated at 40 psi. for 3 hours using the Parr™ apparatus. The mixture was filtered through Celite™ and the filtrate concentrated in vacuo. The residue was taken up in a mixture of 1.0M Hydrochloric acid in diethyl ether (5 ml) and methanol (5 ml) and stirred at reflux for 18 hours. The mixture was concentrated in vacuo to yield the title compound (90 mg, 78%).

Workup

  1. filtrationThe mixture was filtered through Celite™
  2. concentrationthe filtrate concentrated in vacuo
  3. additionThe residue was taken up in a mixture of 1.0M Hydrochloric acid in diethyl ether (5 ml) and methanol (5 ml)
  4. temperatureat reflux for 18 hours
  5. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-dc41e23f69384010bd16d669ea65fa8c
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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