Formaldehyde → HCID 53312154, compound

HRID 924345Notes

Reaction equation

HRID 924345 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.C=O.C1(C)C=CC=CC=1>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 1140TolueneHCID 81531DiisopropylethylamineHCID 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) (10.0 g, 21.9 mmol) is dissolved in 50 mL of anhydrous tetrahydrofuran, add iPr2NEt (3.7 g, 28.5 mmol) anhydrous Lithium chloride (490 mg, 11.0 mmol) and molecular sieves (2.0 g), refluxed for 30 min under nitrogen atmosphere, then add paraformaldehyde (790 mg, 26.3 mmol), reflux for 2 h under nitrogen atmosphere. The reaction mixture is cooled to room temperature, add 100 mL of toluene, filter to remove the molecular sieves, the filtration is washed with 5% HCl(aq) (50 mL*2), saturated Na2CO3 and brine, dry over anhydrous Na2SO4 and concentrate under vacuum to obtain (R)-5-Biphenyl-4-ylmethyl-3-methylene-1-((E)-styryl)-pyrrolidin-2-one (1a, R1=styryl), which is direct used in next step. Spectroscopic data as Example 23, Method 1.

Workup

  1. temperaturerefluxed for 30 min under nitrogen atmosphere
  2. filtrationfilter
  3. customto remove the molecular sieves
  4. filtrationthe filtration
  5. washis washed with 5% HCl(aq) (50 mL*2), saturated Na2CO3 and brine
  6. dry with materialdry over anhydrous Na2SO4
  7. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-3047a0f75e3d4113a99467f63a7b6e03
Source dataset
uspto-grants-2016_03
Patent number
US09278908B2

Reaction notes

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