Ethanol → Ethyl 2-amino-3,3-diethoxypropanoate

HRID 2378940ノート

反応式

HRID 2378940 の反応式
[CH2:1]([O:3][CH:4]([O:14][CH2:15][CH3:16])[CH:5]([N+:11]([O-])=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(O)C.[H][H]>>[NH2:11][CH:5]([CH:4]([O:14][CH2:15][CH3:16])[O:3][CH2:1][CH3:2])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

参加物

4

反応物 3

HCID 702EthanolHCID 10944403Ethyl 3,3-diethoxy-2-nitropropanoateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 11790347Ethyl 2-amino-3,3-diethoxypropanoate収率 92%

実験手順

Ethyl 3,3-diethoxy-2-nitropropanoate (2.45 g, 10.42 mmol) was dissolved in Ethanol (70 mL, 1240 mmol). Nitrogen gas was bubbled through the mixture for 5 minutes. Raney® nickel was added to the mixture. Reaction vessel was placed on a Parr apparatus and charged with 13 psi of hydrogen gas. Reaction shook at room temperature for 1 hour. Mixture was removed from the apparatus and filtered over celite. Filter cake was washed with 150 mL ethanol followed by 250 mL hot ethanol. Filtrate was concentrated to dryness. Title compound was obtained as red oil in 92% yield. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 4.59 (d, J=4.39 Hz, 1 H) 4.05-4.30 (m, 2 H) 3.65-3.81 (m, 2 H) 3.38-3.63 (m, 3 H) 1.87 (s, 2 H) 1.20-1.29 (m, 3 H) 1.12-1.20 (m, 6 H).

後処理

  1. customNitrogen gas was bubbled through the mixture for 5 minutes
  2. additionRaney® nickel was added to the mixture
  3. customReaction vessel
  4. customReaction
  5. customMixture was removed from the apparatus
  6. filtrationfiltered over celite
  7. filtrationFilter cake
  8. washwas washed with 150 mL ethanol
  9. concentrationFiltrate was concentrated to dryness

出典と根拠

ORDレコード
ord-b1f16003f1c2401aa322fc0f975a974a
出典データセット
uspto-grants-2008_12
特許番号
US07470680B2

反応ノート

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