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

HRID 2065851Notes

Reaction equation

HRID 2065851 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-236d06615a8546b2bb79f97b7243e4a3
Source dataset
uspto-grants-2012_10
Patent number
US08288556B2

Reaction notes

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