Methyl Benzoate → HCID 86673650, compound

HRID 924321Notes

Reaction equation

HRID 924321 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]2[N:12]([CH2:13][C:14]3[CH:19]=[CH:18][C:17](OC)=[CH:16][CH:15]=3)[C:11](=[O:22])[CH2:10][CH2:9]2)=[CH:3][CH:2]=1.[CH3:29]C([O-])(C)C.[K+].[C:35](OC)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1(C)C=CC=CC=1>[C:35]([C@@H:10]1[CH2:9][CH:8]([CH2:7][C:4]2[CH:5]=[CH:6][C:1]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:2][CH:3]=2)[N:12](/[CH:13]=[CH:14]/[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:29]=2)[C:11]1=[O:22])(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 7150Methyl BenzoateHCID 23665647Potassium tert-butoxideHCID 53311905HCID 53311905, compound

Product 1

HCID 86673650HCID 86673650, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(S)-5-Biphenyl-4-ylmethyl-1-((E)-styryl)-pyrrolidin-2-one (3a, R1=styryl) (1.00 g, 2.8 mmol) is heated to dissolve in 3 mL of anhydrous toluene under N2, add t-BuOK (0.43 g, 3.7 mmol) in one portion, stir at this temperature for 10 min, then add methyl benzoate dropwise, the reaction mixture reflux overnight, cool to room temperature, quench with saturated NH4Cl aqueous solution, separate the organic phase, extract with toluene (30 mL*3), the combined organic extracts are washed with saturated Na2CO3 aqueous solution and brine, dry over anhydrous Na2SO4 and concentrate under vacuum. The residue is purified by silica gel column chromatography, eluting with 5:1 heptane/ethyl acetate to obtain (S)-3-Benzoyl-5-biphenyl-4-ylmethyl-1-((E)-styryl)-pyrrolidin-2-one (4a, R1=styryl, R4=phenyl), the ratio of (3S,5S) to (3R,5S) is 70:30 as determine by HPLC. Spectroscopic data as Example 8, Method 1.

Workup

  1. customquench with saturated NH4Cl aqueous solution
  2. customseparate the organic phase
  3. extractionextract with toluene (30 mL*3)
  4. washthe combined organic extracts are washed with saturated Na2CO3 aqueous solution and brine
  5. dry with materialdry over anhydrous Na2SO4
  6. concentrationconcentrate under vacuum
  7. customThe residue is purified by silica gel column chromatography
  8. washeluting with 5:1 heptane/ethyl acetate

Sources & evidence

ORD record
ord-60fa39458ae443b99944f209ae9195fe
Source dataset
uspto-grants-2016_03
Patent number
US09278908B2

Reaction notes

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