Ethyl Acetate → (R)-5-phenylmorpholin-2-one

HRID 1971289Notes

Reaction equation

HRID 1971289 reaction equation
[C:1]1([CH:7](Br)[C:8]([O-:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC([CH:18]([NH2:21])[CH2:19][OH:20])=CC=1.C(N(C(C)C)CC)(C)C.CCOC(C)=O>CC#N>[C:1]1([C@H:7]2[NH:21][CH2:18][C:19](=[O:20])[O:10][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 924662-Amino-2-phenylethanolHCID 22017357Bromo(phenyl)acetate

Product 1

HCID 11126817(R)-5-phenylmorpholin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of phenylbromoacetate (18.58 g, 86 mmol) in CH3CN under nitrogen was added a solution of (R)-phenylglycinol (10.17 g, 74 mmol) and di-isopropylethylamine (34 mL, 195 mmol) in CH3CN. The volatiles were removed under reduced pressure keeping the bath temperature below 25° C. to obtain an oil that was treated with EtOAc (120 mL) and stirred for 15 min. The resulting white precipitate was removed by filtration. The filtrate was concentrated under reduced pressure and the desired product was isolated using column chromatography (SiO2) with a step gradient of 10% to 50% [v/v] EtOAc in cyclohexane to give after evaporation (R)-5-phenylmorpholin-2-one EBE 06134 (3.17 g, 24% yield) as a white solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe bath temperature below 25° C.
  3. customto obtain an oil that
  4. customThe resulting white precipitate was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e9c37dc0889c4f7f8d4d856c8c7d1d4a
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

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