Formaldehyde → HCID 15086755, compound

HRID 2107967Notes

Reaction equation

HRID 2107967 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:9][N:8]([CH2:10][C:11]#[CH:12])[C:7](=[O:13])[CH2:6]1)(=[O:3])[CH3:2].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[CH2:20]=O.[OH-].[NH4+]>C(O)(=O)C.O1CCOCC1>[C:1]([O:4][C@@H:5]1[CH2:9][N:8]([CH2:10][C:11]#[C:12][CH2:20][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:7](=[O:13])[CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8082PiperidineHCID 14923Ammonium HydroxideHCID 150466662-Pyrrolidinone, 4-(acetyloxy)-1-(2-propynyl)-, (S)-

Product 1

HCID 15086755HCID 15086755, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.5 g of (S)-4-(acetyloxy)-1-(2-propynyl)-2-pyrrolidinone, 20 ml of dry dioxane, 1.64 ml of piperidine, 0.66 g of paraformaldehyde, 3.0 ml of acetic acid and 42 mg of cupric chloride was stirred for 30 minutes and then heated at reflux for 45 minutes. The mixture was basified to pH 10 with ammonium hydroxide and then extracted with 5×50 ml of dichloromethane. The extracts were combined, dried, filtered and concentrated with toluene in vacuo. The residual oil was chromatographed on deactivated alumina, giving 2.3 g of the desired product as a pale yellow oil [α]D260 =-17° (dichloromethane).

Workup

  1. temperatureheated
  2. temperatureat reflux for 45 minutes
  3. extractionextracted with 5×50 ml of dichloromethane
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated with toluene in vacuo
  7. customThe residual oil was chromatographed on deactivated alumina

Sources & evidence

ORD record
ord-ab36490aad56429291556c829a94af34
Source dataset
uspto-grants-1990_06
Patent number
US04937235

Reaction notes

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