Water → HCID 66841441, compound

HRID 1929017Notes

Reaction equation

HRID 1929017 reaction equation
C([O:3][C:4]([CH:6]1[CH:11]2[CH2:12][O:13][CH2:14][C:15](=O)[N:10]2[CH2:9][CH2:8][CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:12]1[CH:11]2[CH:6]([CH2:4][OH:3])[CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][O:13]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66841436HCID 66841436, compound

Product 1

HCID 66841441HCID 66841441, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 66 (114 mg, 0.5 mmol) in 5 ml of anhydrous THF is added LAH (40 mg, 1.0 mmol) and the mixture refluxed for 9 hours. The mixture is cooled to 0° C. and treated successively with 0.04 ml of water, 3N aqueous sodium hydroxide (0.04 ml, 0.12), and 0.12 ml of water. The mixture is stirred for 15 min. and then extracted three times with DCM. The combined organic phases are dried over anhydrous sodium sulphate and evaporated under educed pressure. The residual pale yellow oil (75 mg) is purified by chromatography (Biotage 12 Si, I=7.5 cm, DCM/MeOH/conc. Ammonia 95:4.5:0.5).

Workup

  1. temperaturethe mixture refluxed for 9 hours
  2. extractionextracted three times with DCM
  3. dry with materialThe combined organic phases are dried over anhydrous sodium sulphate
  4. customevaporated under educed pressure
  5. customThe residual pale yellow oil (75 mg) is purified by chromatography (Biotage 12 Si, I=7.5 cm, DCM/MeOH/conc. Ammonia 95:4.5:0.5)

Sources & evidence

ORD record
ord-4f8bc9ef054a49ce883679f7f55c9e52
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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