Ammonia → (2R-cis)-4-(2-aminoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetic acid

HRID 893497

Reaction equation

HRID 893497 reaction equation
[C:1]([CH2:3][C@H:4]1[O:9][C:8]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[O:7][C@@H:6]([CH2:15][C:16]([OH:18])=[O:17])[CH2:5]1)#[N:2].N.O.[H][H]>CO>[NH2:2][CH2:1][CH2:3][C@H:4]1[O:9][C:8]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[O:7][C@@H:6]([CH2:15][C:16]([OH:18])=[O:17])[CH2:5]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 15045140(+/-)-cis-4-(Cyanomethyl)-1,5dioxaspiro[5.5]undecane-2-acetic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 15045142(2R-cis)-4-(2-aminoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetic acidYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 0.13 g of (±)-cis-4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2-acetic acid in 20 mL of methanol saturated with anhydrous ammonia is added to a Parr shaker bottle containing 0.2 g of water wet Raney nickel #30. The solution is heated at 40° C. and 50 pounds per square inch gage (psig) hydrogen pressure for 17 hours. The suspension is cooled and filtered to remove the Raney nickel through filter aid and the precipitate is washed with methanol. The filtrate is concentrated at reduced pressure The residue is dissolved in methanol saturated with anhydrous ammonia, treated with decolorizing charcoal, filtered through filter aid and evaporated to give 0.13 g of (±)-cis-4-(2-aminoethyl)-1,5-dioxaspiro-[5.5]undecane-2-acetic acid.

Workup

  1. temperatureThe suspension is cooled
  2. filtrationfiltered
  3. customto remove the Raney nickel
  4. filtrationthrough filter aid
  5. washthe precipitate is washed with methanol
  6. concentrationThe filtrate is concentrated at reduced pressure The residue
  7. dissolutionis dissolved in methanol saturated with anhydrous ammonia
  8. additiontreated with decolorizing charcoal
  9. filtrationfiltered
  10. filtrationthrough filter aid
  11. customevaporated

Sources & evidence

ORD record
ord-8fc7cb57060c4562a74e64beede1b88e
Source dataset
uspto-grants-1992_06
Patent number
US05124482

Linked notes

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