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

HRID 2378940Notes

Reaction equation

HRID 2378940 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b1f16003f1c2401aa322fc0f975a974a
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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