Acetic Acid → HCID 21969058, compound

HRID 1420861Notes

Reaction equation

HRID 1420861 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][C:4]=1[C:14]1[CH2:15][O:16][C@:17]2([CH2:23][CH2:22][CH2:21][NH:20][C@H:19]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:18]=1.C(O)(=O)C>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:11])[F:12])=[CH:5][C:4]=1[C@@H:14]1[CH2:18][C@@:17]2([CH2:23][CH2:22][CH2:21][NH:20][C@H:19]2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:16][CH2:15]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 57283671HCID 57283671, compound

Product 1

HCID 21969058HCID 21969058, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of (5R,6S)-3-(2-methoxy-5-trifluoromethoxyphenyl)-6-phenyl-1-oxa-7-aza-spiro[4.5]dec-3-ene (Example 2; 1.4 g), 10% palladium hydroxide/carbon (0.25 g) in methanol (90 ml) containing acetic acid (9 ml) was hydrogenated at 50 psi for 16 h. The solution was filtered, evaporated and the residue was crystallized twice from hexane to give the title compound. m.p. 91-104° C. 1H NMR (250 MHz, CDCl3) δ 7.50-7.54 (2H, m), 7.33-7.36 (3H, m),), 6.90 (1H, dd, J 8.9, 2.07 Hz), 6.68 (1H, d, J 8.9 Hz), 6.17 (1H, d, J 2.7 Hz), 4.08 (1H, t, J 7.8 Hz), 3.75 (1H, m), 3.69 (4H, s+d), 3.24 (1H, bd), 3.12 (1H, dd, J 10.3, 8.03 Hz), 2.82 (1H, td, J 12.4, 2.6 Hz), 2.16-1.80 (6H, m), and 1.55-1.64 (2H, m). m/z (ES+) 408 (M+1).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated
  3. customthe residue was crystallized twice from hexane

Sources & evidence

ORD record
ord-a20eae6cbeed4109a13def20bfdd35b7
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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