Hydrochloric Acid → HCID 53312154, compound

HRID 924344Notes

Reaction equation

HRID 924344 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.CCN(C(C)C)C(C)C.[O-]S([O-])(=O)=O.[Mg+2].C=O.Cl>O1CCCC1.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

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 81531DiisopropylethylamineHCID 86673650HCID 86673650, compound

Product 1

HCID 53312154HCID 53312154, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

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 iPr2NEt (370 mg, 2.8 mmol) anhydrous Lithium chloride (49 mg, 1.1 mmol) and anhydrous MgSO4 (260 mg, 2.2 mmol), reflux for 30 min under nitrogen atmosphere, then add paraformaldehyde (80 mg, 2.7 mmol), reflux for 2 h under nitrogen atmosphere. The reaction mixture is cooled to room temperature, add 20 mL of toluene and 10 mL of 5% HCl(aq), separate the aqueous phase, wash with saturated sodium hydrogen carbonate aqueous solution and brine, dry over anhydrous sodium sulfate and concentrate under vacuum to obtain (R)-5-Biphenyl-4-ylmethyl-3-methylene-1-((E)-styryl)-pyrrolidin-2-one (1a, R1=styryl).

Workup

  1. temperaturereflux for 30 min under nitrogen atmosphere
  2. customseparate the aqueous phase
  3. washwash with saturated sodium hydrogen carbonate aqueous solution and brine
  4. dry with materialdry over anhydrous sodium sulfate
  5. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-6f81ccfd6e374c36becc159845560a7a
Source dataset
uspto-grants-2016_03
Patent number
US09278908B2

Reaction notes

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