Cyclobutanone → HCID 67057789, compound

HRID 2361707Notes

Reaction equation

HRID 2361707 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:12][N:11]([C:13]([CH:15]3[CH2:21][CH2:20][CH2:19][N:18]([C:22](OCC4C=CC=CC=4)=O)[CH2:17][CH2:16]3)=[O:14])[CH2:10]2)=[CH:4][CH:3]=1.[C:32]1(=O)[CH2:35]C[CH2:33]1>CCO.[Pd]>[CH:22]1([N:18]2[CH2:19][CH2:20][CH2:21][CH:15]([C:13]([N:11]3[CH2:10][CH:9]([O:8][C:5]4[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=4)[CH2:12]3)=[O:14])[CH2:16][CH2:17]2)[CH2:35][CH2:32][CH2:33]1

Participants

5

Reactant 2

HCID 14496CyclobutanoneHCID 67057850HCID 67057850, compound

Product 1

HCID 67057789HCID 67057789, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl 4-({3-[(6-methylpyridin-3-yl)oxy]azetidin-1-yl}carbonyl)azepane-1-carboxylate (37 mg, 87 μmol), cyclobutanone (13 μl, 0.18 mmol) and 5% Pd/C (5 mg) in EtOH (4 ml) were stirred under a hydrogen atmosphere for 12 hours. The reaction was then filtered over celite and concentrated. The residue was dissolved in EtOAc (30 ml) and washed with water (3×15 ml), dried (MgSO4), filtered and concentrated. The residue was purified by silica FCC (using a gradient of eluents; 98:2:1 to 90:10:1 DCM/MeOH/2M NH3 in MeOH) to give the title product as colourless oil (12 mg, 40%).

Workup

  1. filtrationThe reaction was then filtered over celite and
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc (30 ml)
  4. washwashed with water (3×15 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica FCC (

Sources & evidence

ORD record
ord-52ad167605fd4a1fbb68a282f490fbf0
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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