Morpholine → 4-[(5-Bromofuran-2-yl)methyl]morpholine

HRID 396170Notes

Reaction equation

HRID 396170 reaction equation
[Br:1][C:2]1[O:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.C(O)(=O)C>[Br:1][C:2]1[O:6][C:5]([CH2:7][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 6003285-Bromofuran-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 124786874-[(5-Bromofuran-2-yl)methyl]morpholineYield 84%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-bromo-2-furaldehyde (1.76 g) and morpholine (1.00 ml) in 40 mL anhydrous THF at room temperature was added acetic acid (0.60 mL) followed by sodium triacetoxyborohydride (3.28 g). The mixture was stirred at room temperature for 3 h and then poured into a saturated solution of sodium bicarbonate (100 mL). After stirring vigorously for 5 min the layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated to dryness. Purification of the residue by flash chromatography afforded 2.09 g (8.49 mmol, 84% yield) of 4-(5-bromo-2-furylmethyl)morpholine.

Workup

  1. stirringAfter stirring vigorously for 5 min the layers
  2. customwere separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-cc910059ba6546b0b36980cb6fa2d865
Source dataset
uspto-grants-2003_08
Patent number
US06608052B2

Reaction notes

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