Sodium Methoxide → (S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholine-3-yl]ethanol

HRID 16379Notes

Reaction equation

HRID 16379 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[NH:13][C@@H:12]([C@@H:14]([O:16]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH3:15])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[NH:13][C@@H:12]([C@@H:14]([OH:16])[CH3:15])[CH2:11][O:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 673717534-nitrobenzoic acid (S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholin-3-yl]ethyl ester

Product 1

HCID 68716014(S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholine-3-yl]ethanolYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-nitrobenzoic acid (S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholine-3-yl]ethyl ester (1.46 g mg) in methanol (40 mL) was added sodium methoxide (1.9 mL, 28% methanol solution), and the resultant solution was stirred at room temperature for 1 hour. Solvent was removed by distillation under reduced pressure, and the resultant product was diluted with ethyl acetate and water. The organic layer was partitioned and washed with brine. The organic layer was then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/3), to thereby obtain the titled compound (833 mg). The physical properties of the compound were as follows.

Workup

  1. customSolvent was removed by distillation under reduced pressure
  2. additionthe resultant product was diluted with ethyl acetate and water
  3. customThe organic layer was partitioned
  4. washwashed with brine
  5. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  6. customSolvent was removed by distillation under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/3)

Sources & evidence

ORD record
ord-4672f9afed6343d68d2fd65325dc70cb
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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