Toluene → 1-((Benzyloxy)carbonyl)-3-methylpiperidine-2-carboxylic acid

HRID 60882

Reaktionsgleichung

Reaktionsgleichung von HRID 60882
Cl.[CH3:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH:4]1[C:9]([OH:11])=[O:10].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].C1(C)C=CC=CC=1>[OH-].[Na+].C1COCC1>[CH2:16]([O:15][C:13]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([CH3:2])[CH:4]1[C:9]([OH:11])=[O:10])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 10387Benzyl chloroformateHCID 696193093-Methylpiperidine-2-carboxylic acid hydrochloride

Produkt 1

HCID 666248731-((Benzyloxy)carbonyl)-3-methylpiperidine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 20445995Sodium hydroxide tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-Methylpiperidine-2-carboxylic acid hydrochloride (28.5 g, 31.6 mmol) was dissolved in (1:1) 2 M NaOH/THF (600 mL) and cooled to 0° C. Benzyl chloroformate (31.57 ml, 222 mmol) was then added dropwise and the reaction was stirred overnight. Toluene was then added and organic layer discarded to remove unreacted chloroformate. The aqueous layer was made acidic (pH=2) with conc. HCl and the product was extracted with EtOAc, dried (MgSO4), and concentrated in vacuo to give a crude residue which was used without further purification (41.6 g, 94.5%). 1H NMR (CDCl3, 400 MHz) δ 7.40-7.37 (m, 5H), 5.19 (m, 2H), 4.95-4.72 (m, 1H), 4.14-4.03 (m, 1H), 3.36-3.25 (m, 1H), 1.93-1.53 (m, 5H), 1.20-1.05 (m, 3H).

Aufarbeitung

  1. customto remove unreacted chloroformate
  2. extractionthe product was extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0409c044ad724af4a04c943f9ed3440b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440982B2

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