Formaldehyde → HCID 68714094, compound

HRID 1021045Notes

Reaction equation

HRID 1021045 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]2[N:12]([C:13](=O)C(C)(C)C)[C:11](=[O:19])[C@H:10]([CH3:20])[CH2:9]2)=[CH:3][CH:2]=1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.C=O>C(O)C>[C:1]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]2[N:12]([CH2:13][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[C:11](=[O:19])[C@H:10]([CH3:20])[CH2:9]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 66738857(3R,5S)-5-biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-3-methylpyrrolidin-2-one

Product 1

HCID 68714094HCID 68714094, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3R,5S)-5-biphenyl-4-ylmethyl-3-methylpyrrolidin-2-one (2-a, R1=H) (1 g, 3.8 mmol) is added to ethanol (7 ml). Pyrrolidine (312 μl, 3.8 mmol) and aqueous formaldehyde (393 μl, 5.3 mmol) are added. The mixture is heated at reflux for 3 h. The mixture is next cooled to room temperature and concentrated in vacuo to afford (3R,5S)-5-biphenyl-4-ylmethyl-3-methyl-1-pyrrolidin-1-ylmethylpyrrolidin-2-one (2-a, R1=methylpyrrolidin). Spectroscopic data as reported in Example 19.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51a219ad05834b9080c498e1132e560c
Source dataset
uspto-grants-2014_05
Patent number
US08716495B2

Reaction notes

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