Toluene → HCID 86673650, compound

HRID 924319Notes

Reaction equation

HRID 924319 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.[H-].[Na+].[C:31](OC)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[C:41]1(C)C=CC=CC=1>>[C:31]([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:41]=2)[C:11]1=[O:22])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 7150Methyl BenzoateHCID 24758Sodium hydrideHCID 53311905HCID 53311905, compound

Product 1

HCID 86673650HCID 86673650, compound

Procedure

(S)-5-Biphenyl-4-ylmethyl-1-((E)-styryl)-pyrrolidin-2-one (3a, R1=styryl) (50.0 g, 141.7 mmol) is heated to dissolve in 140 mL of anhydrous toluene under N2, add sodium hydride (8.04 g, 184.2 mmol) in portions, stir at this temperature for 10 min, then add methyl benzoate dropwise, reflux for 6 h, cool to room temperature, quench with saturated NH4Cl aqueous solution, separate the organic phase, extract with toluene (100 mL*3), the combined organic extracts are washed with saturated Na2CO3 aqueous solution and brine, dry over anhydrous Na2SO4 and concentrate under vacuum 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. 1HNMR (400 MHz, CDCl3): 2.35 (m, 1H, 3-CHH), 3.26 (m, 3H, 5-CH2+3-CHH), 3.74 (m, 1H, 2-CH), 4.32 (m, 1H, 4-CH), 6.21 (m, 1H, C═CHH), 7.21˜7.80 (m, 20H, aromatic+C═CHH).

Workup

  1. customquench with saturated NH4Cl aqueous solution
  2. customseparate the organic phase
  3. extractionextract with toluene (100 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

Sources & evidence

ORD record
ord-455fbbfdf231401d8f963032aeb9d456
Source dataset
uspto-grants-2016_03
Patent number
US09278908B2

Reaction notes

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