HCID 22860775, compound → HCID 10811257, compound

HRID 1956492Notes

Reaction equation

HRID 1956492 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([O:14][CH2:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)[C@H:9]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)C1C=CC=CC=1>C(O)C.O.[Pd]>[F:29][C:26]([F:27])([F:28])[C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:19]=1)[CH2:15][O:14][C@H:10]1[O:11][CH2:12][CH2:13][NH:8][C@@H:9]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 1

HCID 22860775HCID 22860775, compound

Product 1

HCID 10811257HCID 10811257, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3.6 g (7.27 mmol) of 4-benzyl-2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(R)-phenylmorpholine in 100 mL of ethanol and 5 mL of water, containing 0.72 g of 10% Pd/C was hydrogenated on a Parr apparatus for 36 h. The catalyst was filtered and thoroughly washed with EtOAc. The filtrate was concentrated and the residue was partitioned between water and EtOAc. The EtOAc layer was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography using a gradient of 10-60% EtOAc/hexane to isolate 2.05 g (70%) of 2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(R)-phenylmorpholine. 1H NMR (CDCl3) 1.92 (br s, 1H), 2.91 (m, 1H), 3.05 (td, J=11Hz and 3 Hz, 1H), 3.68 (d, J=7 Hz, 1H), 3.81 (td, J=11 Hz and 3 Hz, 1H), 4.01 (m, 1H), 4.44 (d, J=7 Hz), 4.5 (d, J=13 Hz, 1H), 4.85 (d, J=13 Hz, 1 H), 7.28-7.42 (m, 7H), 7.67 (s, 1H).

Workup

  1. filtrationThe catalyst was filtered
  2. washthoroughly washed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. customthe residue was partitioned between water and EtOAc
  5. washThe EtOAc layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-095c0484d04d46b3bc4ac82227ee947d
Source dataset
uspto-grants-1998_07
Patent number
US05780467

Reaction notes

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