Triethylamine → HCID 58315456, compound

HRID 1483121Notes

Reaction equation

HRID 1483121 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:13][CH:12]([OH:14])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(CC)CC.[CH3:22][C:23]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])[CH3:24].CCOC(C)=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:23]([Si:26]([CH3:28])([CH3:27])[O:14][CH:12]1[CH2:11][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[N:9][CH:8]=2)[CH2:13]1)([CH3:25])([CH3:24])[CH3:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 592909581-(6-Nitro-pyridin-3-yl)-azetidin-3-olHCID 86584982Sodium bicarbonate ethyl acetate

Product 1

HCID 58315456HCID 58315456, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(6-nitro-pyridin-3-yl)-azetidin-3-ol (154 mg, 0.779 mmol) in 2 mL of DMF is added Et3N (0.2 mL, 0.15 mmol), TBDMSCl (117 mg, 0.776 mmol). The resulting mixture is stirred at room temperature for 2 h. Poured into EtOAc/NaHCO3. the aqueous layer is extracted with ethyl acetate (2×50 mL). The combined organic layers are ished with brine, dried over Na2SO4. Concentrated to give 5-[3-(tert-butyl-dimethyl-silanyloxy)-azetidin-1-yl]-2-nitro-pyridine (175 mg, 73%).

Workup

  1. extractionthe aqueous layer is extracted with ethyl acetate (2×50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationConcentrated

Sources & evidence

ORD record
ord-5b8ec5766b014b4f956a96a7466aaa87
Source dataset
uspto-grants-2016_08
Patent number
US09416136B2

Reaction notes

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