Formaldehyde → HCID 53312154, compound

HRID 924342Notes

Reaction equation

HRID 924342 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.C=O.C([O-])([O-])=O.[K+].[K+]>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

5

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 86673650HCID 86673650, compound

Product 1

HCID 53312154HCID 53312154, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

(S)-3-Benzoyl-5-biphenyl-4-ylmethyl-1-((E)-styryl)-pyrrolidin-2-one (4a, R1=styryl, R4=phenyl) (1.0 g, 2.2 mmol) is dissolved in 5 mL of anhydrous tetrahydrofuran, add 37% formaldehyde aqueous solution (0.36 mL, 4.4 mmol), 1 M K2CO3 aqueous solution (4.4 mL, 4.4 mmol) and n-Bu4NOH (12 mg, 0.05 mmol), heat to 40° C. for 2 h. The reaction mixture is cooled to room temperature, extract with ethyl acetate, the extracts are washed with saturated Na2CO3 aqueous solution and brine, dry over anhydrous Na2SO4 and concentrate under vacuum, the residue 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 reaction mixture is cooled to room temperature
  2. extractionextract with ethyl acetate
  3. washthe extracts are washed with saturated Na2CO3 aqueous solution and brine
  4. dry with materialdry over anhydrous Na2SO4
  5. concentrationconcentrate under vacuum
  6. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-6ae1b668961443ff8b74b6be8025c1fe
Source dataset
uspto-grants-2016_03
Patent number
US09278908B2

Reaction notes

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