Morpholine → HCID 66636594, compound

HRID 2190250Notes

Reaction equation

HRID 2190250 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CCOC(C)=O>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 13854Pyrrole-2-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66636594HCID 66636594, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1H-pyrrole-2-carbaldehyde (5.0 g, 52.5 mmol) and morpholine (5.0 mL, 57.8 mmol) in CH2Cl2 (160 mL) was added sodium triacetoxyborohydride (12.2 g, 57.8 mmol). The mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with EtOAc (200 mL). The organic phase was washed with aqueous NaHCO3 and brine then dried (MgSO4), filtered and concentrated to dryness. The residue was purified by column chromatography (silica, 0-10% MeOH in CH2Cl2) to afford the sub-title compound (5.3 g, 61%).

Workup

  1. washThe organic phase was washed with aqueous NaHCO3 and brine
  2. dry with materialthen dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by column chromatography (silica, 0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-47f6eb618ba84548913f4470a973828a
Source dataset
uspto-grants-2012_12
Patent number
US08324264B1

Reaction notes

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