Diethyl Ether → HCID 57309346, compound

HRID 728890Notes

Reaction equation

HRID 728890 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[C@H:18]([CH:19]=[CH:20][CH2:21][CH2:22][C:23](OCC)=[O:24])[CH2:17][O:16][C:15]1([CH3:29])[CH3:28])=[O:13])([CH3:10])([CH3:9])[CH3:8].C(OCC)C.S([O-])(O)(=O)=O.[K+]>O>[C:7]([O:11][C:12]([N:14]1[C@H:18]([CH:19]=[CH:20][CH2:21][CH2:22][CH2:23][OH:24])[CH2:17][O:16][C:15]1([CH3:29])[CH3:28])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 57155621HCID 57155621, compound

Product 1

HCID 57309346HCID 57309346, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.7 g of lithium aluminium hydride are added in portions at 0°-2° to a solution of 23.5 g of 2 according to b) in 550 mlof absolute diethyl ether. After stirring at 0°-2° for 3 hours, a solution of 25 g of potassium hydrogen sulphate in 250 ml of water is added dropwise with cooling. The mixture is filtered through Celite® and washed thoroughly with diethyl ether. The organic phase iswashed twice with 200 ml of 1N hydrochloric acid each time and twice with 250 ml of 10% sodium bicarbonate solution each time. The aqueous phases are extracted twice with 100 ml of ether each time. The organic phases arewashed with 20% sodium chloride solution, dried over sodium sulphate and concentrated by evaporation. Chromatography on silica gel using hexane/ethyl acetate as eluant yields 18.6 g of 3, [α]D =-10.1° (c=1.4, CHCl3); C15H27NO4 ; calculated: 63.13%, H 9.54%, N 4.91%; found: C 63.0%, H 9.5%, N 5.0%.

Workup

  1. temperaturewith cooling
  2. filtrationThe mixture is filtered through Celite®
  3. washwashed thoroughly with diethyl ether
  4. extractionThe aqueous phases are extracted twice with 100 ml of ether each time
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-79fd25d461334039af989f190c34fafe
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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