Methanol → Methyl 1-amino-1-cyclopentanecarboxylate, HCl

HRID 276253

Reaktionsgleichung

Reaktionsgleichung von HRID 276253
[NH2:1][C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.O=S(Cl)[Cl:12].[CH3:14]O>>[ClH:12].[NH2:1][C:2]1([C:7]([O:9][CH3:14])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 2901CycloleucineHCID 24386Thionyl Chloride

Produkt 1

HCID 11513856Methyl 1-amino-1-cyclopentanecarboxylate, HClAusbeute 100 %

Versuchsvorschrift

To a suspension of 1-aminocyclopentanecarboxylic acid, (675 g, 5.23 mol, 1.0 equiv.) in MeOH (6.5 L) held at −15° C. with an ice/MeOH bath was added SOCl2 (687 mL, 9.4 mol, 1.8 equiv.), dropwise at such a rate that the reaction temp. did not exceed 7° C. After the addition was complete, cooling was removed, the reaction was allowed to stir at room temp. overnight, then was concentrated under reduced pressure. The residue was treated with CH2Cl2 (1 L) and concentrated under reduced pressure to afford methyl 1-aminocyclopentanecarboxylate HCl salt as a white solid (938 g, 100%): 1H NMR (CD3OD) d 1.87-1.94 (m, 8H), 3.83 (s, 3H); NMR (DMSO-d6) δ1.67-1.71 (m, 2H), 1.83-1.98 (m, 4H), 2.06-2.14 (m, 2H), 3.73 (s, 3H), 8.81 (br s 3). This material was used in the next step without further purification.

Aufarbeitung

  1. customheld at −15° C. with an ice/MeOH bath
  2. customdid not exceed 7° C
  3. additionAfter the addition
  4. temperaturecooling
  5. customwas removed
  6. concentrationwas concentrated under reduced pressure
  7. additionThe residue was treated with CH2Cl2 (1 L)
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1df1160096ee462089613b8be482eaf8
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353006B1

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