HCID 58547762, compound → HCID 58547782, compound

HRID 454912Notes

Reaction equation

HRID 454912 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([O:13][CH:14]3[CH2:17][N:16](C(OCC4C=CC=CC=4)=O)[CH2:15]3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1>[OH-].[OH-].[Pd+2].CCO>[NH:16]1[CH2:15][CH:14]([O:13][C:8]2[C:7]([CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[N:12][CH:11]=[CH:10][N:9]=2)[CH2:17]1

Participants

4

Reactant 1

HCID 58547762HCID 58547762, compound

Product 1

HCID 58547782HCID 58547782, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a N2 purged round bottom flask was added benzyl 3-(3-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yloxy)azetidine-1-carboxylate (see PREPARATION P28.2; 490 mg, 1.334 mmol), pearlman's catalyst (37.5 mg, 0.267 mmol) and EtOH (10 mL). A balloon of H2 was placed atop the round bottom flask. After 20 hours, the reaction was filtered through CELITE® and the cake was washed with EtOAc. The filtrate was concentrated in vacuo to give 2-(azetidin-3-yloxy)-3-(tetrahydro-2H-pyran-4-yl)pyrazine (240 mg, 1.020 mmol, 76% yield), as a tan residue. MS (ESI) m/z 236.1 (MH+).

Workup

  1. filtrationthe reaction was filtered through CELITE®
  2. washthe cake was washed with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b54bb1f747f14624b8fac5875d251695
Source dataset
uspto-grants-2013_07
Patent number
US08497265B2

Reaction notes

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