Diethyl Ether → HCID 59371551, compound

HRID 2095414Notes

Reaction equation

HRID 2095414 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:24]=[N:25][CH:26]=[C:27]([O:29][CH2:30][C@@H:31]3[CH2:34][CH2:33][N:32]3[C:35](OC(C)(C)C)=O)[CH:28]=2)[CH2:19][CH2:18]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[O-]S([O-])(=O)=O.[Na+].[Na+].CCOCC>C1COCC1.O>[CH2:7]([O:14][CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19][N:20]([C:23]2[CH:24]=[N:25][CH:26]=[C:27]([O:29][CH2:30][C@@H:31]3[CH2:34][CH2:33][N:32]3[CH3:35])[CH:28]=2)[CH2:21][CH2:22]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 59371653HCID 59371653, compound

Product 1

HCID 59371551HCID 59371551, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (45 mg, 1.2 mmol, 5.0 equiv.) in THF (1.5 mL) was added a solution of 3-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]pyridine (115 mg, 0.24 mmol) in THF (0.5 mL). The mixture was refluxed for 1 h, then cooled to room temperature. To a flask containing 4-5 g of Na2SO4 was added with stirring 40-50 mL of Et2O followed by the cooled reaction mixture. Water was subsequently added dropwise to quench residual hydride. When no more gas was generated, the mixture was filtered, and the solid phase was washed with CH2Cl2/MeOH 4:1 (100-150 mL). Solvent removal furnished crude 3-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]-5-[(1-methyl-2(S)-azetidinyl)methoxy]pyridine (97 mg, 100%), which was used in the following step without purification.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. additionwas added
  3. customfollowed by the cooled reaction mixture
  4. customto quench residual hydride
  5. filtrationthe mixture was filtered
  6. washthe solid phase was washed with CH2Cl2/MeOH 4:1 (100-150 mL)
  7. customSolvent removal

Sources & evidence

ORD record
ord-cfc953b7949a46c68cc5340919ab5000
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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