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

HRID 1198352

反応式

HRID 1198352 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ba5003c934f54fdcba1a786b9f414507
出典データセット
uspto-grants-1994_01
特許番号
US05280126

関連ノート

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