Morpholine → HCID 58356368, compound

HRID 244631Notes

Reaction equation

HRID 244631 reaction equation
[CH:1]([C:3]1[N:7]([CH:8]([CH3:10])[CH3:9])[N:6]=[C:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH: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>[CH3:9][CH:8]([N:7]1[C:3]([CH2:1][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:4][C:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:6]1)[CH3:10]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86655907HCID 86655907, compound

Product 1

HCID 58356368HCID 58356368, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,1-Dimethylethyl 5-formyl-1-(1-methylethyl)-1H-pyrazole-3-carboxylate (118 mg) was dissolved in anhydrous DCM (10 ml), morpholine (0.048 ml) was added and the mixture was stirred under nitrogen for 2 h at RT. Sodium triacetoxyborohydride (210 mg) was added and the mixture was stirred at RT for 18 h. Sodium bicarbonate solution (20 ml) and DCM (20 ml) were added and separated then the aqueous layer was re-extracted with DCM (2×20 ml) and separated by hydrophobic frit. The combined organic layers were concentrated in vacuo and the residue was purified by flash chromatography on silica gel (20 g silica) eluting with a gradient of 0-100% ethyl acetate in cyclohexane over 20 mins to give the title compound (101 mg) as a white solid.

Workup

  1. stirringthe mixture was stirred at RT for 18 h
  2. customseparated
  3. extractionthe aqueous layer was re-extracted with DCM (2×20 ml)
  4. customseparated by hydrophobic frit
  5. concentrationThe combined organic layers were concentrated in vacuo
  6. customthe residue was purified by flash chromatography on silica gel (20 g silica)
  7. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane over 20 mins

Sources & evidence

ORD record
ord-143c66f383a64ba882f3e0419d12dcd8
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

Loading…