HCID 69429233, compound → HCID 22940603, compound

HRID 1352671Notes

Reaction equation

HRID 1352671 reaction equation
[C:1]1(/[CH:7]=[CH:8]\[C@@H:9]2[CH2:25][N:13]3[CH2:14][CH2:15][N:16]([C:18]4[N:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=4)[CH2:17][C@@H:12]3[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>[Pd].C(O)C>[C:1]1([CH2:7][CH2:8][C@H:9]2[CH2:25][N:13]3[CH2:14][CH2:15][N:16]([C:18]4[N:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=4)[CH2:17][C@@H:12]3[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 69429233HCID 69429233, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22940603HCID 22940603, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.15 g (0.44 mmol) of Z-(7R,9aS)-7-(2-phenyl)ethenyl-2-(5-fluoropyrimidin-2-yl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine, 0.015 g of 10% palladium on carbon and 25 mL of ethanol was shaken under 40 psig of hydrogen gas in a Parr apparatus for 6 h. The mixture was filtered through Celite, and the filtrate concentrated to give 0.124 g (83%) of (7R,9aS)-7-(2-phenyl)ethyl-2-(5-fluoropyrimidin-2-yl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine. mp (.HCl) 250–252° C. HRMS calcd for C20H26FN4O (MH+): 341.2142, found: 341.2126.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-72cbc46320e0446b8130359db2de6d8a
Source dataset
uspto-grants-2007_05
Patent number
US07220753B2

Reaction notes

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