HCID 59215904, compound → HCID 59215849, compound

HRID 2245456Notes

Reaction equation

HRID 2245456 reaction equation
[F:1][CH2:2][C@@H:3]1[CH2:12][N:11]2[C@H:6]([CH2:7][O:8][CH2:9][CH2:10]2)[CH2:5][N:4]1CC1C=CC=CC=1>CC(O)=O.[Pd]>[F:1][CH2:2][C@@H:3]1[CH2:12][N:11]2[C@H:6]([CH2:7][O:8][CH2:9][CH2:10]2)[CH2:5][NH:4]1

Participants

4

Reactant 1

HCID 59215904HCID 59215904, compound

Product 1

HCID 59215849HCID 59215849, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of (7S,9aS)-7-(fluoromethyl)-8-(phenylmethyl) octahydropyrazino[2,1-c][1,4]oxazine (D128, 30 mg, 0.11 mmol) in AcOH (30 ml) was added Pd-black (12 mg, 0.11 mmol) and the reaction mixture was stirred under a H2 atmosphere (5 atm.) for 1.5 hrs. The reaction mixture was filtered on a SCX cartridge washing with methanol and then with 2M methanolic ammonia. The fractions eluted with ammonia were combined and evaporated to dryness. The crude was purified by chromatography (silica, CH2Cl2:MeOH 1:0 to 8:2) to give the title compound (14.9 mg, y=78%).

Workup

  1. filtrationThe reaction mixture was filtered on a SCX cartridge
  2. washwashing with methanol
  3. washThe fractions eluted with ammonia
  4. customevaporated to dryness
  5. customThe crude was purified by chromatography (silica, CH2Cl2:MeOH 1:0 to 8:2)

Sources & evidence

ORD record
ord-6765c066feaa4c4aaca08ab25a3f67b3
Source dataset
uspto-grants-2010_03
Patent number
US07683056B2

Reaction notes

Loading…