Formaldehyde → HCID 53312154, compound

HRID 2179538Notes

Reaction equation

HRID 2179538 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.[Li+].[Cl-].C=O>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

7

Reactant 4

HCID 712FormaldehydeHCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 86673650HCID 86673650, compound

Product 1

HCID 53312154HCID 53312154, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-5-Biphenyl-4-ylmethyl-3-(2,2-dimethyl-propionyl)-1-((E)-styryl)-pyrrolidin-2-one (4a, R1=t-butoxycarbonyl, R4=t-butyl) (2.7 g, 6.2 mmol) is dissolved in 10 mL of anhydrous tetrahydrofuran, add iPr2NEt (1.1 g, 8.2 mmol), anhydrous LiCl (140 mg, 3.2 mmol) and molecular sieves (0.5 g), the mixture is refluxed under nitrogen atmosphere for 30 min, then add paraformaldehyde (230 mg, 7.6 mmol) in one portion, reflux for 2 h, cool to room temperature, add 50 mL of toluene, filtere, the filtration is washed with 10% HCl(aq), saturated Na2CO3 and brine, dry over anhydrous NaSO4, evaporate 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). Stepectroscopic data as Example 23, Method 1.

Workup

  1. temperaturethe mixture is refluxed under nitrogen atmosphere for 30 min
  2. filtrationfiltere, the filtration
  3. washis washed with 10% HCl(aq), saturated Na2CO3 and brine
  4. dry with materialdry over anhydrous NaSO4
  5. customevaporate under vacuum
  6. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-bf7c1005e5af4a36b7d2b4abd83efa63
Source dataset
uspto-grants-2015_06
Patent number
US09067883B2

Reaction notes

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