Sodium Hydroxide → HCID 11858316, compound

HRID 1710763Notes

Reaction equation

HRID 1710763 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][CH:18]=[C:19]([CH2:21][C:22]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=O)[N:20]=2)=[CH:12][CH:11]=1.B.O1CCCC1.[OH-].[Na+].[Cl-].[NH4+]>O1CCCC1>[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][CH:18]=[C:19]([CH2:21][CH2:22][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[N:20]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 2723981Borane;tetrahydrofuranHCID 59457505HCID 59457505, compound

Product 1

HCID 11858316HCID 11858316, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-[(2-{4-[2-(2-methylpyrrolidin-1-yl)ethoxy]phenyl}-1,3-oxazol-4-yl)acetyl]piperidine i54 (0.13 g, 0.33 mmol, 1 eq) in tetrahydrofuran (5 ml) is treated with borane-tetrahydrofuran complex (1.0 M in tetrahydrofuran, 1.3 ml, 1.3 mmol, 4 eq) and the resulting mixture is refluxed overnight. A 2 N sodium hydroxide solution is added to reach pH 10 and the mixture is refluxed for 6 h. A saturated solution of aqueous ammonium chloride is added and the solution is extracted two times with ethyl acetate. The organic layers are dried over magnesium sulfate, filtered and concentrated under vacuum. Purification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 96/3.6/0.4) gives 0.115 g of 1-[2-(2-{4-[2-(2-methylpyrrolidin-1-yl)ethoxy]phenyl}-1,3-oxazol-4-yl)ethyl]piperidine 121.

Workup

  1. temperaturethe resulting mixture is refluxed overnight
  2. temperaturethe mixture is refluxed for 6 h
  3. extractionthe solution is extracted two times with ethyl acetate
  4. dry with materialThe organic layers are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 96/3.6/0.4)

Sources & evidence

ORD record
ord-c465326610784bfdb10cc6954154787a
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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