Tin atom → HCID 20027817, compound

HRID 653502Notes

Reaction equation

HRID 653502 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[CH:8]2[CH2:11][C:6]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=3)([CH2:7]2)[C:5]1=[O:21])[CH:2]=[CH2:3].[Sn]>O.Cl>[CH2:1]([N:4]1[C:9](=[O:10])[CH:8]2[CH2:11][C:6]([C:12]3[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=3)([CH2:7]2)[C:5]1=[O:21])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 5352426Tin atomHCID 200278163-Allyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

Product 1

HCID 20027817HCID 20027817, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A mixture of 1.97 g of 3-allyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione and 5.2 g of tin powder in 14 ml of water and 14 ml of concentrated hydrochloric acid is stirred at 100° for 1.5 hours. After cooling to room temperature, the reaction mixture is diluted with a little water, filtered and rendered alkaline by the addition of sodium hydroxide solution. The reaction mixture is extracted with ethyl acetate, and the organic phase is washed neutral with dilute sodium chloride solution, dried over magnesium sulphate and concentrated by evaporation. Melting point 176°-178° (from ethyl acetate/petroleum ether).

Workup

  1. filtrationfiltered
  2. additionby the addition of sodium hydroxide solution
  3. extractionThe reaction mixture is extracted with ethyl acetate
  4. washthe organic phase is washed neutral with dilute sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-9d502c679d404609a7d09d45550f7dfd
Source dataset
uspto-grants-1987_06
Patent number
US04677129

Reaction notes

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