Diethyl Ether → HCID 59371262, compound

HRID 2095413Notes

Reaction equation

HRID 2095413 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[CH2:35][CH2:34][CH2:33][NH:32]3)[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+].[CH3:43]COCC>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[CH2:35][CH2:34][CH2:33][N:32]3[CH3:43])[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 59371492HCID 59371492, compound

Product 1

HCID 59371262HCID 59371262, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (60 mg, 1.59 mmol, 5.0 equiv.) in THF (5 mL) was added a solution of 3-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]-5-[(2(S)-pyrrolidinyl)methoxy]pyridine (156 mg, 0.32 mmol) in THF (1 mL). The mixture was refluxed for 1.5 h and then cooled to room temperature. To a flask containing 4-5 g of Na2SO4 was added with stirring 40-50 mL of ether 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)-pyrrolidinyl)methoxy]pyridine (106 mg, 81%), which could be used in the following step without further purification.

Workup

  1. temperatureThe mixture was refluxed for 1.5 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-46c3512b80bf4312b46d53667b2bdc25
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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