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

HRID 2378940노트

반응식

HRID 2378940 반응식
[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]

참가 물질

4

반응물 3

HCID 702EthanolHCID 10944403Ethyl 3,3-diethoxy-2-nitropropanoateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 11790347Ethyl 2-amino-3,3-diethoxypropanoate수율 92%

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b1f16003f1c2401aa322fc0f975a974a
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470680B2

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