Formaldehyde → HCID 53312154, compound

HRID 924336Notes

Reaction equation

HRID 924336 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.CC(C)([O-])C.[K+].C=O.O>O1CCCC1>[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

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86673650HCID 86673650, compound

Product 1

HCID 53312154HCID 53312154, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 tetrahydrofuran, add potassium tert-butoxide (161 mg, 1.4 mmol) and paraformaldehyde (66 mg, 2.2 mmol) in one portion, the result mixture is heated to reflux for 2 h under nitrogen atmosphere. The reaction mixture is cooled to room temperature, add 15 mL of water, 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 the crude product which is purified by column chromatography to obtain (R)-5-Biphenyl-4-ylmethyl-3-methylene-1-((E)-styryl)-pyrrolidin-2-one (1a, R1=styryl). Spectroscopic data as Example 23, Method 1.

Workup

  1. temperaturethe result mixture is heated
  2. temperatureto reflux for 2 h under nitrogen atmosphere
  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
  7. customto obtain the crude product which
  8. customis purified by column chromatography

Sources & evidence

ORD record
ord-835ea4a2b10844cb8be4727aac396f55
Source dataset
uspto-grants-2016_03
Patent number
US09278908B2

Reaction notes

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