HCID 68689093, compound → HCID 11206703, compound

HRID 1159087Notes

Reaction equation

HRID 1159087 reaction equation
C([N:8]1[CH2:22][CH:21]([CH3:23])[N:11]2[C:12](=[O:20])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[CH2:19][CH:10]2[CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].CCOC(C)=O>[CH3:23][C@H:21]1[N:11]2[C:12](=[O:20])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[CH2:19][C@@H:10]2[CH2:9][NH:8][CH2:22]1

Participants

5

Reactant 2

HCID 68689093HCID 68689093, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11206703HCID 11206703, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1,2,3,4,11,11a-Hexahydro-2-benzyl-4-methyl-pyrazino[1,2-b]isoquinolin-6-one (from Isomer B, 93 mg, 0.30 mmol) and 10% palladium on carbon (40 mg) in EtOAc (9 ml) was stirred under a balloon of hydrogen. After 3 days the reaction was about 60% complete by HPLC. The catalyst was filtered off and then fresh catalyst added. After stirring an additional day under a balloon of hydrogen, the reaction was filtered through Celite® rinsing with EtOAc and methanol to afford 56 mg of crude product. Column purification (Chiralcel OD, 15% 1/1 MeOH/EtOH in hexanes) afforded pure (4R,11aR)-1,2,3,4,11,11a-hexahydro-4-methyl-pyrazino[1,2-b]isoquinolin-6-one (18 mg, 28% yield). MS (ESI) 217 (M+H). Further elution afforded pure (4S,11aS)-1,2,3,4,11,11a-hexahydro-4-methyl-pyrazino[1,2-b]isoquinolin-6-one (16 mg, 25% yield). MS (ESI) 217 (M+H).

Workup

  1. filtrationThe catalyst was filtered off
  2. additionfresh catalyst added
  3. filtrationthe reaction was filtered through Celite®
  4. washrinsing with EtOAc and methanol
  5. customto afford 56 mg of crude product
  6. customColumn purification (Chiralcel OD, 15% 1/1 MeOH/EtOH in hexanes)

Sources & evidence

ORD record
ord-6cb926cd2308419d9f9c63df18dee5ca
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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