HCID 58504420, compound → HCID 58504672, compound

HRID 2367597Notes

Reaction equation

HRID 2367597 reaction equation
I[CH2:2][C@H:3]1[O:8][CH2:7][C@@H:6]([CH3:9])[N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4]1>C(O)C.[Pd]>[CH3:2][C@H:3]1[O:8][CH2:7][C@@H:6]([CH3:9])[N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4]1

Participants

4

Reactant 1

HCID 58504420HCID 58504420, compound

Product 1

HCID 58504672HCID 58504672, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of (2S,5R)-2-(iodomethyl)-5-methyl-4-(phenylmethyl)morpholine (5.0 g, 15.10 mmol) in ethanol (120 mL) stirred under nitrogen at room temperature was added Pd/C (1.607 g, 1.510 mmol) in ethanol (120 mL). The reaction mixture was purged with hydrogen, and was stirred under hydrogen at 25° C. for 2 hours. After the completion (by LCMS), the mixture was filtered through a pad of celite, the filtrate was purified by silica gel chromatography (300-400 mesh), eluting with petroleum/EtOAc (1:1) to afford the desired title compound (2.5 g) as a white solid. LC-MS (ES) m/z=206 [M+H]+. 1H NMR (CDCl3): δ 7.96-7.93 (m, 2H), 7.49-7.46 (m, 3H), 4.69-4.61 (m, 2H), 4.41-4.37 (m, 1H), 4.03-3.97 (m, 1H), 3.73-3.70 (d, J=12.8 Hz, 1H), 3.48-3.46 (d, J=6.4 Hz, 1H), 3.27-3.24 (d, J=12.4 Hz, 2H), 2.78-2.69 (m, 1H), 1.39-1.37 (d, J=6.4 Hz, 3H), 1.24-1.23 (d, J=12.4 Hz, 3H).

Workup

  1. customThe reaction mixture was purged with hydrogen
  2. filtrationAfter the completion (by LCMS), the mixture was filtered through a pad of celite
  3. customthe filtrate was purified by silica gel chromatography (300-400 mesh)
  4. washeluting with petroleum/EtOAc (1:1)

Sources & evidence

ORD record
ord-fac5d99cf49d4bb7a8103f5f20aca807
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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