Triphenylphosphine → HCID 68310297, compound

HRID 1021307Notes

Reaction equation

HRID 1021307 reaction equation
[OH:1][CH:2]1[CH2:5][N:4](C(OCC2C=CC=CC=2)=O)[CH2:3]1.[C:16]([O:20][C:21]1[N:26]=[CH:25][C:24](O)=[CH:23][CH:22]=1)([CH3:19])([CH3:18])[CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(C)C=CC=CC=1>C1COCC1>[NH:4]1[CH2:3][CH:2]([O:1][C:24]2[CH:23]=[CH:22][C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:26][CH:25]=2)[CH2:5]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 10081755Benzyl 3-hydroxyazetidine-1-carboxylateHCID 72222662HCID 72222662, compoundHCID 178459888HCID 178459888, compound

Product 1

HCID 68310297HCID 68310297, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

Benzyl 3-hydroxyazetidine-1-carboxylate (2.3 g) and 6-tert-butoxypyridin-3-ol (1.5 g) were mixed with THF (25 ml), and triphenylphosphine (4 g) was added thereto. A 1.9 M DIAD/toluene solution (8 ml) was added dropwise thereto, followed by stirring at 55° C. overnight. The reaction mixture was concentrated under reduced pressure. The obtained residue was mixed with ethanol (25 ml), and 10% palladium carbon (800 mg) were added thereto, followed by stirring at room temperature for 5 hours under hydrogen atmosphere. The reaction mixture was filtered using Celite as a filtration adjuvant, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain 5-(azetidin-3-yloxy)-2-tert-butoxypyridine (595 mg).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe obtained residue was mixed with ethanol (25 ml), and 10% palladium carbon (800 mg)
  4. additionwere added
  5. stirringby stirring at room temperature for 5 hours under hydrogen atmosphere
  6. filtrationThe reaction mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-afa0ff41d2c74245bde7a56f68a30f07
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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