Sodium hydride → HCID 86683226, compound

HRID 1852158Notes

Reaction equation

HRID 1852158 reaction equation
[H-].[Na+].[O:3]1[CH2:6][CH:5]([OH:7])[CH2:4]1.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15](=O)[O:16]C1C=CC=CN=1>C1COCC1.CCOC(C)=O>[C:15](=[O:16])([O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][N:8]=1)[O:7][CH:5]1[CH2:6][O:3][CH2:4]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2757370Carbonic acid di-2-pyridyl esterHCID 9942117Oxetan-3-ol

Product 1

HCID 86683226HCID 86683226, compoundYield 17.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride, 60% in mineral oil (0.594 g, 14.85 mmol) in THF (50 mL) was added oxetan-3-ol (1 g, 13.50 mmol) at 0° C. After stirring 30 min, the solution was transferred to a solution of di(pyridin-2-yl)carbonate (2.92 g, 13.50 mmol) in THF (50 mL) through a cannula. The formed slurry was stirred at 0° C. for 30 min. The slurry was warmed to rt and stirred for 2 h. The reaction was diluted with EtOAc, washed with brine, dried over MgSO4, filtered, concentrated to give a residue that was purified by Biotage eluting with 20-50% EtOAc in hexanes to afford the desired product oxetan-3-yl pyridin-2-yl carbonate (452 mg, 17.16% yield) as an oil. 500 mg sm recovered. 1H NMR (400 MHz, CHLOROFORM-d) d 8.42 (dd, J=4.6, 1.6 Hz, 1H), 7.89-7.77 (m, 1H), 7.33-7.27 (m, 1H), 7.14 (d, J=8.3 Hz, 1H), 5.62-5.52 (m, 1H), 4.96-4.91 (m, 2H), 4.83-4.78 (m, 2H).

Workup

  1. stirringThe formed slurry was stirred at 0° C. for 30 min
  2. stirringstirred for 2 h
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue that
  8. customwas purified by Biotage
  9. washeluting with 20-50% EtOAc in hexanes

Sources & evidence

ORD record
ord-eb7b854e56ef4394a9ba302e2947cdfc
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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