Formaldehyde → HCID 53312154, compound

HRID 2179539Notes

Reaction equation

HRID 2179539 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.N1CCOCC1>CO>[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 8083MorpholineHCID 86673650HCID 86673650, compound

Product 1

HCID 53312154HCID 53312154, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Biphenyl-4-ylmethyl-2-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (4a, R1=t-butoxycarbonyl, R4=hydroxyl) (3.95 g, 10.0 mmol) is dissolved in 10 mL of methanol, add paraformaldehyde (0.60 g, 20.0 mmol) and morpholine (1.05 g, 12.0 mmol), the mixture is heated to refluxed for 2 h under nitrogen atmosphere, cool to room temperature, evaporate the solvent under vacuum, the residue is dissolved in 50 mL of ethyl acetate, ish with 1% HCl(aq), 10% sodium hydrogen carbonate(aq) and brine, dry over anhydrous sodium sulfate and concentrate under vacuum to obtain (R)-5-Biphenyl-4-ylmethyl-3-methylene-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (1a, R1=t-butoxycarbonyl).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto refluxed for 2 h under nitrogen atmosphere
  3. customevaporate the solvent under vacuum
  4. dissolutionthe residue is dissolved in 50 mL of ethyl acetate, ish with 1% HCl(aq), 10% sodium hydrogen carbonate(aq) and brine
  5. dry with materialdry over anhydrous sodium sulfate
  6. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-8e4646c4fb2a449a90d0d1f0810c47d9
Source dataset
uspto-grants-2015_06
Patent number
US09067883B2

Reaction notes

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