Ammonia → HCID 15045168、化合物

HRID 5710

反応式

HRID 5710 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]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:5]1)#[N:2].N.[H][H]>CO.O>[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]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:5]1

参加物

6

反応物 3

HCID 222AmmoniaHCID 15045166(+/-)-cis-1,1-Dimethylethyl 4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2acetateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 15045168HCID 15045168、化合物収率 97.9%

試薬・触媒・溶媒 2

HCID 962Water触媒HCID 887Methanol溶媒

実験手順

A solution of 1.19 g of (±)-cis-1,1-dimethylethyl 4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2-acetate in 30 mL of methanol saturated with gaseous ammonia is treated with 0.3 g of Raney nickel #30 and hydrogen gas in a shaker at 50 pounds per square inch gage (psig) and 40° C. After 22 hours, thin layer chromatography indicates no starting nitrile present. The suspension is cooled, filtered through filter aid, and concentrated to an oil. This crude oil is purified by silica gel flash chromatography (30:20:1; ethyl acetate:methanol:ammonium hydroxide) to give 1.18 g of (±)-cis-1,1-dimethylethyl 4-(2-aminoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetate as a clear oil which solidifies upon standing.

後処理

  1. temperatureThe suspension is cooled
  2. filtrationfiltered
  3. filtrationthrough filter aid
  4. concentrationconcentrated to an oil
  5. customThis crude oil is purified by silica gel flash chromatography (30:20:1; ethyl acetate:methanol:ammonium hydroxide)

出典と根拠

ORDレコード
ord-59c9df81cc2c43c7970479ad5cc29ef6
出典データセット
uspto-grants-1993_09
特許番号
US05245047

関連ノート

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