Water → HCID 66841559, compound

HRID 1929020Notes

Reaction equation

HRID 1929020 reaction equation
C([O:3][C:4]([CH:6]1[CH:10]2[CH2:11][O:12][CH2:13][C:14](=O)[N:9]2[CH2:8][CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:11]1[CH:10]2[CH:6]([CH2:4][OH:3])[CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][O:12]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66841605HCID 66841605, compound

Product 1

HCID 66841559HCID 66841559, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 69 (1.1 g, 5.0 mmol) in 50 ml of anhydrous THF are added LAH (400 mg, 10 mmol) and the mixture refluxed for 18 hours. The mixture is cooled to 0° C. and treated successively with 0.4 ml of water, 0.4 ml of 3N aq. sodium hydroxide, and 1.2 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. The residual yellow oil (880 mg) is purified by chromatography (Silica gel 60, 0.063-0.2 mesh, DCM/MeOH/conc. ammonia 90:9:1).

Workup

  1. temperaturethe mixture refluxed for 18 hours
  2. extractionextracted three times with DCM
  3. dry with materialThe combined organic phases are dried over anhydrous sodium sulphate
  4. customevaporated
  5. customThe residual yellow oil (880 mg) is purified by chromatography (Silica gel 60, 0.063-0.2 mesh, DCM/MeOH/conc. ammonia 90:9:1)

Sources & evidence

ORD record
ord-77aad443ffc44a4182d41d2e8b6cf113
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

Loading…