Ethyl Acetate → HCID 67490806, compound

HRID 1917415Notes

Reaction equation

HRID 1917415 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[CH2:13]([C@H:16]1[C@H:20]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:19][N:18]([C@@H:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH3:31])[C:17]1=O)[CH:14]=[CH2:15].O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[CH2:13]([C@H:16]1[C@H:20]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:27])[CH3:28])([CH3:24])[CH3:25])[CH2:19][N:18]([C@@H:30]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH3:31])[CH2:17]1)[CH:14]=[CH2:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 2724148Sodium potassium tartrate tetrahydrateHCID 16684438Red-AlHCID 67490756HCID 67490756, compound

Product 1

HCID 67490806HCID 67490806, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
45 °C

Procedure

A 65% solution of Red-Al™ in toluene (788 mL, 2.63 mol) was added dropwise to a solution of (3S,4S)-3-allyl-4-(tert-butyldimethylsilyloxy)methyl-2-oxo-1-[(1R)-1-phenylethyl]pyrrolidine (327 g, 875 mmol) in toluene (1500 mL) in a nitrogen atmosphere over one hour. The reaction solution was stirred at 45° C. for five hours and then cooled to 0° C., and a 20% (+)-potassium sodium tartrate tetrahydrate solution (2.00 L) was added. The reaction solution was poured into a mixture of ethyl acetate and brine, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1→4:1) to give 213 g of the title compound as a colorless syrup.

Workup

  1. temperaturecooled to 0° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1→4:1)

Sources & evidence

ORD record
ord-6fbd60bc795e4c72bbdb5b5a1281036a
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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