Tetrahydrofuran → HCID 18318102, compound

HRID 1700259Notes

Reaction equation

HRID 1700259 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:20][N:21]=[N+]=[N-])([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.O>[C:1]([N:8]1[CH2:9][CH2:10][C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)([CH2:20][NH2:21])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 18318096HCID 18318096, compound

Product 1

HCID 18318102HCID 18318102, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 25-mL, round-bottomed flask was charged with Intermediate 1c (0.259 g, 0.803 mmol), 8 mL of THF, and triphenylphosphine (0.32 g, 0.884 mmol). The mixture was stirred at room temperature for 3.5 h and then 0.10 mL of water was added. The resulting reaction mixture was stirred at room temperature for 66 h, and then diluted with ethyl acetate and water. The layers were separated, and the organic phase was washed with water and saturated sodium chloride solution, dried over potassium carbonate, filtered and concentrated. The crude product was purified by column chromatography (gradient elution: 1:4 ethyl acetate-hexane, 9:1 ethyl acetate-methanol, and then 100% methanol) to give the free amine (0.063 g) as a clear oil.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at room temperature for 66 h
  3. customThe layers were separated
  4. washthe organic phase was washed with water and saturated sodium chloride solution
  5. dry with materialdried over potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (
  9. washgradient elution

Sources & evidence

ORD record
ord-47fe24ec899848c78f5962cd483d7b39
Source dataset
uspto-grants-2002_02
Patent number
US06350760B1

Reaction notes

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