Water → HCID 20529836, compound

HRID 1660180Notes

Reaction equation

HRID 1660180 reaction equation
[CH3:1][C:2]1([CH3:10])[CH:8]2[CH2:9][CH:3]1[CH2:4][CH2:5][C:6]2=O.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][C:2]1([CH3:10])[CH:8]2[CH2:9][CH:3]1[CH2:4][CH:5]=[C:6]2[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 32735Nopinone

Product 1

HCID 20529836HCID 20529836, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A solution of 30 g of nopinone ([α]D20 =+39.90; c=8 in ethanol), 29 g of pyrrolidine and 0.4 g of p-toluene-sulfonic acid in 150 ml anhydrous benzene was heated at reflux for 40 h under nitrogen atmosphere in a vessel fitted with a water separator. After evaporation of the solvent and distillation of the residue, there were obtained 39.5 g (95% yield) of 1-(6,6-dimethylnorpin-2en-2-yl)-pyrrolidine having b.p. 117°-118° C./10 Torr.

Workup

  1. temperatureat reflux for 40 h under nitrogen atmosphere in a vessel
  2. customAfter evaporation of the solvent and distillation of the residue

Sources & evidence

ORD record
ord-f3326f1f37364b1b9f8dbf3224de6385
Source dataset
uspto-grants-1981_12
Patent number
US04307122

Reaction notes

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