Morpholine → HCID 58356406, compound

HRID 244629Notes

Reaction equation

HRID 244629 reaction equation
[CH:1]([C:3]1[CH:7]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[N:5]([CH:15]([CH3:17])[CH3:16])[N:4]=1)=O.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:16][CH:15]([N:5]1[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:7][C:3]([CH2:1][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[N:4]1)[CH3:17]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58356347HCID 58356347, compound

Product 1

HCID 58356406HCID 58356406, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,1-Dimethylethyl 3-formyl-1-(1-methylethyl)-1H-pyrazole-5-carboxylate (491 mg) was dissolved in anhydrous DCM (20 ml), morpholine (0.198 ml) was added and the mixture was stirred under nitrogen for 2 h at RT. Sodium triacetoxyborohydride (873 mg) was added and the mixture was stirred at RT for 18 h. Sodium bicarbonate solution (50 ml) and DCM (50 ml) were added and separated and the aqueous layer was re-extracted with DCM (2×50 ml) and separated by hydrophobic frit. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel (50 g silica), eluting with a gradient of 0-100% ethyl acetate in cyclohexane over 30 mins to give the title compound (628 mg) as a colourless oil.

Workup

  1. stirringthe mixture was stirred at RT for 18 h
  2. customseparated
  3. extractionthe aqueous layer was re-extracted with DCM (2×50 ml)
  4. customseparated by hydrophobic frit
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash chromatography on silica gel (50 g silica)
  7. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane over 30 mins

Sources & evidence

ORD record
ord-544a35d50dce4abaa3cb390c2f47004f
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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