Hydrochloric Acid → 1-((Tert-butoxy)carbonyl)-4-(methoxycarbonyl)piperidine-4-carboxylic acid

HRID 655946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655946
[N:1]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6][CH2:5][C:4]([C:11]([O:13]C)=[O:12])([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.[Li+].[OH-].Cl>C1COCC1.CO>[C:18]([O:17][C:15]([N:1]1[CH2:2][CH2:3][C:4]([C:7]([O:9][CH3:10])=[O:8])([C:11]([OH:13])=[O:12])[CH2:5][CH2:6]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 579202841-Tert-butyl 4,4-dimethyl piperidine-1,4,4-tricarboxylate

Produkt 1

HCID 579202821-((Tert-butoxy)carbonyl)-4-(methoxycarbonyl)piperidine-4-carboxylic acidAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1-tert-butyl 4,4-dimethyl piperidine-1,4,4-tricarboxylate (6.2 g, 20.5 mmol) in THF (11 mL) and CH3OH (11 mL) was added aqueous LiOH (2 N, 11 mL, 22 mmol, 1.1 equiv.). The reaction mixture was stirred at 80° C. for 1 h. The reaction mixture was neutralized with HCl (1N) and was concentrated to dryness. The residue was dissolved in ethyl acetate and dried over Na2SO4 and concentrated to give 1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidine-4-carboxylic acid (4.7 g, 80%), which was used without further purification. LRMS (M+H+-Boc) m/z 188.0.

Aufarbeitung

  1. concentrationwas concentrated to dryness
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0eb8ca6bc06144f494b88536b05791b2
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071625B2

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