Ammonium formate → HCID 69291358, compound

HRID 899096Notes

Reaction equation

HRID 899096 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([OH:26])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH:8]1[CH2:13][CH2:12][O:11][C@@H:10]([C@:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([OH:26])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:23])[F:24])[CH2:9]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59693636HCID 59693636, compound

Product 1

HCID 69291358HCID 69291358, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(4-Benzyl-morpholin-2-yl)-1-phenyl-2-(2-trifluoromethyl-phenyl)-ethanol (352 mg, 1 equiv.) in ethanol (15 mL) at room temperature under nitrogen atmosphere was added ammonium formate (507 mg g, 10 equiv.) followed by addition of palladium on charcoal (10%, 355 mg.). The reaction mixture was heated to reflux for 1 hour, cooled to room temperature and then filtered through Celite. All volatiles were evaporated under vacuum to give 265 mg of the title compound as white solid (94%). The enantiomeric mixture was resolved using chiral HPLC, to give the title compound as a single enantiomer. 1H NMR (300 MHz, CDCl3) δ: 2.25-2.30 (m, 1H), 2.56-2.64 (m, 1H), 2.75-2.87 (m, 2H), 3.18 (d, 1H, J=14.88 Hz), 3.71-3.81 (m, 2H), 3.89 (d, 1H, J=14.88 Hz), 4.02-4.05 (m, 1H), 6.83-6.86 (m, 1H), 7.09-7.34 (m, 7H), 7.53-7.55 (m, 1H) ppm. LCMS (12 minute method) [M+H]+=352 @ Rt 4.73 min. single peak.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. filtrationfiltered through Celite
  4. customAll volatiles were evaporated under vacuum

Sources & evidence

ORD record
ord-9693bee15e93453ca8a273038a994f62
Source dataset
uspto-grants-2008_04
Patent number
US07354920B2

Reaction notes

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