Ethyl Acetate → HCID 86759215, compound

HRID 987934Notes

Reaction equation

HRID 987934 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11](CC(OCC)=O)[O:10][C:9]1([CH3:27])[CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.[C:38](OCC)(=[O:40])[CH3:39].O.O.O.O.C([C@@H]([C@H](C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.O>[C:1]([O:5][C:6]([N:8]1[C:12]([CH2:39][CH:38]=[O:40])([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:11][O:10][C:9]1([CH3:27])[CH3:26])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 1654536381-59-5HCID 21225700DiisobutylaluminumhydrideHCID 69853659HCID 69853659, compound

Product 1

HCID 86759215HCID 86759215, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 4-benzyl-5-ethoxycarbonylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (30 g, 80 mol) in dry toluene (500 ml) was stirred at −78° C. during the addition of of 1M diisobutyl aluminium hydride in toluene (105 ml, 105 mmol). The resulting mixture was stirred at −78° C. for 4 hours and then ethyl acetate (60 ml) was added. After 30 minutes, the resulting mixture was allowed to warm to room temperature and a solution of potassium sodium L-tartrate tetrahydrate (90 g, mmol) in water (350 ml) was added. The resulting biphasic mixture was stirred until the two phases were clear. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried (anhydrous magnesium sulfate) and concentrated in vacuo to provide 4-benzyl-2,2-dimethyl-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester which solidified upon standing overnight.

Workup

  1. waitAfter 30 minutes
  2. temperatureto warm to room temperature
  3. stirringThe resulting biphasic mixture was stirred until the two phases
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried (anhydrous magnesium sulfate)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ccdf96fac674c9fb4b2dbc464e95389
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

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