Sodium hydride → HCID 86683227, compound

HRID 1852167Notes

Reaction equation

HRID 1852167 reaction equation
[H-].[Na+].[CH3:3][C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][O:6][CH2:5]1.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18](=[O:26])[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1>C1COCC1.CCOC(C)=O.[Cl-].[Na+].O>[C:18](=[O:19])([O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=1)[O:10][C:4]1([CH3:3])[CH2:9][CH2:8][CH2:7][O:6][CH2:5]1.[C:18](=[O:26])([O-:17])[O:19][C:20]1[C:25]([C:4]2([CH3:3])[CH2:9][CH2:8][CH2:7][O:6][CH2:5]2)=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

8

Reactant 3

HCID 24758Sodium hydrideHCID 2757370Carbonic acid di-2-pyridyl esterHCID 1225380035906-74-2

Product 2

HCID 70978327HCID 70978327, compoundHCID 86683227HCID 86683227, compoundYield 34.1%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of sodium hydride, 60% in mineral oil (207 mg, 5.17 mmol) in THF (20 mL) was added 3-methyltetrahydro-2H-pyran-3-ol (500 mg, 4.30 mmol) at 0° C. After stirring 30 min, the solution was transferred to a solution of di(pyridin-2-yl)carbonate (931 mg, 4.30 mmol) in THF (20 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 followed by brine. The organic layer was collected, dried over MgSO4, filtered and evaporated to give the crude material. the crude material was purified via biotage (40 g column, 5-40% EtOAc:Hex) to give the expected product 3-methyltetrahydro-2H-pyran-3-ylpyridin-2-yl carbonate (173 mg, 17.94% yield) as a clear thick oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 8.50-8.30 (m, 1H), 7.89-7.74 (m, 1H), 7.27-7.22 (m, 1H), 7.14 (d, J=8.3 Hz, 1H), 4.22-4.05 (m, 1H), 3.88-3.74 (m, 1H), 3.60-3.49 (m, 1H), 3.44 (d, J=12.0 Hz, 1H), 2.38-2.20 (m, 1H), 2.03-1.88 (m, 1H), 1.84-1.72 (m, 1H), 1.63-1.57 (m, 1H), 1.56 (s, 3H).

Workup

  1. stirringThe formed slurry was stirred at 0° C. for 30 min
  2. stirringstirred for 2 h
  3. customThe organic layer was collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude material
  8. customthe crude material was purified via biotage (40 g column, 5-40% EtOAc:Hex)

Sources & evidence

ORD record
ord-b1a81ff7712a4636a2e1369c0e20f2f8
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

Loading…