Hydrochloric Acid → trans-1-Tert-butoxycarbonyl-4-methyl-piperidine-3-carboxylic acid

HRID 1808707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808707
C([O:3][C:4]([CH:6]1[CH:11]([CH3:12])[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]1)=[O:5])C.CO.[OH-].[Li+].Cl>O1CCCC1>[C:16]([O:15][C:13]([N:8]1[CH2:9][CH2:10][C@@H:11]([CH3:12])[C@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)=[O:14])([CH3:17])([CH3:18])[CH3:19]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 3939Lithium HydroxideHCID 707916011-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate

Produkt 1

HCID 86317481trans-1-Tert-butoxycarbonyl-4-methyl-piperidine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a flask containing (+/−)-4-methyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (1.12 g, 4.1 mmol; from example 8 above) was taken up in tetrahydrofuran (12 mL) and methanol (3 mL) and cooled to 0° C. (ice bath). A solution of lithium hydroxide (4.5 mL, 1M) was added and the mixture was warmed to ambient over 3 hours. Extra methanol (2 mL) was added and the material was heated to 60° C. (oil bath) for 5.5 hours. The mixture was cooled to ambient and treated with 1N hydrochloric acid solution (4.7 mL) with vigorous stirring. The solvent was stripped and the remainder was dried under high vacuum for several hours, providing 1.06 g of mainly trans-(+/−)-4-methyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester: as a off-white solid. MS (M−H)−=242.

Aufarbeitung

  1. temperaturethe mixture was warmed
  2. temperatureThe mixture was cooled to ambient and
  3. customthe remainder was dried under high vacuum for several hours

Quellen und Nachweise

ORD-Eintrag
ord-f99dfc6952de45fd920a9ba89c447e36
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08361962B2

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