Formaldehyde → HCID 53312154, compound

HRID 924335Notes

Reaction equation

HRID 924335 reaction equation
[C:1]([C@@H:9]1[CH2:13][CH:12]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[N:11](/[CH:27]=[CH:28]/[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:10]1=[O:35])(=O)C1C=CC=CC=1.[H-].[Na+].C=O>C1(C)C=CC=CC=1>[C:18]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:17]=[CH:16][C:15]([CH2:14][C@H:12]2[N:11](/[CH:27]=[CH:28]/[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:10](=[O:35])[C:9](=[CH2:1])[CH2:13]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 24758Sodium hydrideHCID 86673650HCID 86673650, compound

Product 1

HCID 53312154HCID 53312154, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(S)-3-Benzoyl-5-biphenyl-4-ylmethyl-1-((E)-styryl)-pyrrolidin-2-one (4a, R1=styryl, R4=phenyl) (0.50 g, 1.1 mmol) is dissolved in 2 mL of anhydrous toluene, add sodium hydride (65 mg, 1.5 mmol) in portions then paraformaldehyde (66 mg, 2.2 mmol) in one portion, the result mixture is heat to reflux for 4 h under nitrogen atmosphere. The reaction mixture is cooled to room temperature, then quench with saturated NH4Cl aqueous solution, extract with toluene, the organic extracts are washed with saturated Na2CO3 aqueous solution and brine, dry over anhydrous Na2SO4, evaporate the solvent under vacuum to obtain (R)-5-biphenyl-4-ylmethyl-3-methylene-1-((E)-styryl)-pyrrolidin-2-one (1a, R1=styryl) which could be used in next step directly. 1HNMR (400 MHz, CDCl3): 2.68 (m, 2H, 3-CHH+5-CH2H), 2.81 (m, 1H, 3-CHH), 3.28 (m, 1H, 5-CH2H), 4.32 (m, 1H, 4-CH), 5.35 (s, 1H, C═CHH), 6.04 (s, 1H, C═CHH), 6.23 (d, 1H, C═CHH), 7.21˜7.72 (m, 15H, aromatic+C═CHH).

Workup

  1. temperatureto reflux for 4 h under nitrogen atmosphere
  2. customquench with saturated NH4Cl aqueous solution
  3. extractionextract with toluene
  4. washthe organic extracts are washed with saturated Na2CO3 aqueous solution and brine
  5. dry with materialdry over anhydrous Na2SO4
  6. customevaporate the solvent under vacuum

Sources & evidence

ORD record
ord-361c21c6fe254dfaa35e3a6a99777f91
Source dataset
uspto-grants-2016_03
Patent number
US09278908B2

Reaction notes

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