Ethyl Acetate → 3-(1-Aminoethyl)-3-hydroxypyrrolidine-1-carboxylic acid benzyl ester

HRID 10349

Reaktionsgleichung

Reaktionsgleichung von HRID 10349
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][C:13]2([O:15][CH:14]2[CH3:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.[OH-].[NH4+:26]>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][C:13]([CH:14]([NH2:26])[CH3:16])([OH:15])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 21041146Benzyl 2-methyl-1-oxa-5-azaspiro[2.4]heptane-5-carboxylate

Produkt 1

HCID 690686403-(1-Aminoethyl)-3-hydroxypyrrolidine-1-carboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 2-methyl-1-oxa-5-azaspiro[2,4]heptane-5-carboxylic acid benzyl ester (Example A9, 0.31 g, 1.25 mmol) in methanol (10 mL) and ammonium hydroxide (7 mL) is heated in a sealed tube at 100° C. for 16 hours. After cooling, the reaction mixture is dissolved ethyl acetate, washed with water, dried over Na2SO4 and evaporated to afford the title compound (0.340 g). 1H NMR (200 MHz, CDCl3): δ 7.33–7.26 (m, 5H), 5.28 (bs, 2H), 5.07 (s, 2H), 3.56–3.16 (m, 5H), 2.03–1.76 (m, 2H), 1.15 (d, 3H).

Aufarbeitung

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-25d841ff62cf41b6862babb19ab9536f
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094780B1

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