HCID 57270309, compound → HCID 57243150, compound

HRID 1417554Notes

Reaction equation

HRID 1417554 reaction equation
C(OC([CH2:11][NH:12][C@H:13]1[CH2:38][CH2:37][C@:15]2([O:19][CH2:18][C@H:17]([C:20]3[CH:25]=[C:24]([N:26]4[CH:30]=[CH:29][N:28]=[C:27]4[C:31]([F:34])([F:33])[F:32])[CH:23]=[CH:22][C:21]=3[O:35][CH3:36])[CH2:16]2)[C@@H:14]1[C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1)=O)C1C=CC=CC=1>C(O)C.C(O)(=O)C.[OH-].[Pd+2].[OH-]>[CH3:11][NH:12][C@H:13]1[CH2:38][CH2:37][C@:15]2([O:19][CH2:18][C@H:17]([C:20]3[CH:25]=[C:24]([N:26]4[CH:30]=[CH:29][N:28]=[C:27]4[C:31]([F:33])([F:34])[F:32])[CH:23]=[CH:22][C:21]=3[O:35][CH3:36])[CH2:16]2)[C@@H:14]1[C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1

Participants

5

Reactant 1

HCID 57270309HCID 57270309, compound

Product 1

HCID 57243150HCID 57243150, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

(3S,5R,6R,7S)-7-(N-(Benzyloxycarbonyl)methylamino)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]nonane (7.0 mg, 0.011 mmol) in 0.30 mL of ethanol and 0.24 mL of acetic acid was hydrogenated on the Parr shaker at 47 psi, using 2.3 mg of 20% palladium(II) hydroxide on carbon. After 3 h, the mixture was filtered through 0.45 micron filter and the filtrate was evaporated. The residue was taken in 2.0 mL of ethyl acetate and washed with 1.0 mL of saturated aqueous sodium bicarbonate followed by 1.0 mL of brine. Drying over sodium sulfate and evaporation gave N-methyl((3S,5R,6R,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]non-7-yl)amine. 1NMR (400 MHz, CD3OD): δ7.45 (dd, 2H, J=9, 6 Hz ), 7.29 (d, 1H, J=1 Hz ), 7.21 (d, 1H, J=1 Hz ), 7.19 (dd, 1H, J=9, 2 Hz ), 7.01 (t, 2H, J=9 Hz ), 7.00 (d, 1H, J=9 Hz ), 6.58 (d, 1H, J=2 Hz ), 4.12-4.00 (m, 2H), 3.84-3.75 (m, 1H), 3.79 (s, 3H), 3.13 (d, 1H, J=10 Hz ), 3.05 (t, 1H, J=8 Hz ), 2.54-2.42 (m, 1H), 2.52 (s, 3H), 2.28 (dd, 1H, J=13, 8 Hz ), 2.27-2.20 (m, 1H), 2.07 (ddd, 1H, J=13, 10, 9 Hz ), 1.91 (dd, 1H, J=13, 11 Hz ), 1.90-1.80 (m, 1H). Mass spectrum (NH3/CI): m/z=490.1 (M+1).

Workup

  1. filtrationthe mixture was filtered through 0.45 micron
  2. filtrationfilter
  3. customthe filtrate was evaporated
  4. washwashed with 1.0 mL of saturated aqueous sodium bicarbonate
  5. dry with materialDrying over sodium sulfate and evaporation

Sources & evidence

ORD record
ord-84edc54bfce54622b90b3c7352be51e5
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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