Formaldehyde → HCID 15086755, compound

HRID 1710118Notes

Reaction equation

HRID 1710118 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]D26° =-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-cd80bb87ee2148e0b21e3a0139d5d988
Source dataset
uspto-grants-1990_08
Patent number
US04952600

Reaction notes

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