Tin atom → HCID 20027817, compound

HRID 1722873Notes

Reaction equation

HRID 1722873 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-8303e8aa617f41ac817278d2f06887b9
Source dataset
uspto-grants-1989_08
Patent number
US04857660

Reaction notes

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