Tetrahydropyran-2-methanol → HCID 59525784, compound

HRID 385867Notes

Reaction equation

HRID 385867 reaction equation
[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][OH:10].[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18]Br)[N:13]=1>C1COCC1.O.C(Cl)Cl>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:10][CH2:9][CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][O:3]2)[N:13]=1

Participants

7

Reactant 3

HCID 7524Tetrahydropyran-2-methanolHCID 24758Sodium hydrideHCID 129547962-Bromo-6-(bromomethyl)pyridine

Product 1

HCID 59525784HCID 59525784, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (63.8 mg, 1.59 mmol) in THF (4 mL) at 0° C. under argon was added tetrahydro-2H-pyran-2-ylmethanol (92.5 mg, 0.80 mmol). The mixture was maintained at 0° C. for 20 minutes, at which time 2-bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (200 mg, 0.80 mmol) was added. The reaction allowed to warm to room temperature and then heated to 55° C. overnight. The reaction was then cooled to ambient temperature and quenched by the addition of water. The quenched reaction mixture was diluted with water (10 mL) and DCM (10 mL) and shaken. The suspensions were passed through disposable phase separators and the DCM eluent was captured and evaporated to dryness to afford the title compound which was used without further purification.

Workup

  1. additionwas added
  2. temperatureheated to 55° C. overnight
  3. temperatureThe reaction was then cooled to ambient temperature
  4. customquenched by the addition of water
  5. customThe quenched reaction mixture
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-39ec7825dc864784ab26d7beb3fe1bb8
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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