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

HRID 360022

반응식

HRID 360022 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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
  7. dissolutionThe residue is dissolved in methanol saturated with anhydrous ammonia
  8. additiontreated with decolorizing charcoal
  9. filtrationfiltered
  10. filtrationthrough filter aid
  11. customevaporated

출처 및 근거

ORD 기록
ord-7808c816b96844ee8740d34f9fc8f5f9
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05003080

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