Sodium Hydroxide → 1-(tert-butoxycarbonyl)-4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)piperidine-4-carboxylic acid

HRID 880901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 880901
[I:1][C:2]1[C:6]([CH2:7][C:8]2([C:21]([O:23]CC)=[O:22])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:5][N:4]([CH:26]([CH3:28])[CH3:27])[N:3]=1.[OH-].[Na+]>CO>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][C:8]([CH2:7][C:6]2[C:2]([I:1])=[N:3][N:4]([CH:26]([CH3:27])[CH3:28])[CH:5]=2)([C:21]([OH:23])=[O:22])[CH2:9][CH2:10]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 674915631-tert-butyl 4-ethyl 4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)piperidine-1,4-dicarboxylate

Produkt 1

HCID 674914961-(tert-butoxycarbonyl)-4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)piperidine-4-carboxylic acidAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-tert-butyl 4-ethyl 4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)piperidine-1,4-dicarboxylate (455 mg, 0.9 mmol) in methanol (20 mL) was added 2 N NaOH (5 mL). After stirring for 18 hours at room temperature, the methanol was removed under reduced pressure and the resultant slurry was taken up in 20 mL water, acidified with 2 N HCl and extracted with ethyl acetate (2×30 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to yield 1-(tert-butoxycarbonyl)-4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)piperidine-4-carboxylic acid (430 mg) as a colorless solid. −APCI (M−H) 476.1; 1H NMR (400 MHz, CDCl3, δ): 7.11 (s, 1H), 4.45 (dquin, J=13.4, 6.7 Hz, 1H), 3.95 (br. s., 2H), 2.91 (m, 2H), 2.69 (s, 2H), 2.08 (m, 2H), 1.47 (m, 8H).

Aufarbeitung

  1. customthe methanol was removed under reduced pressure
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d8bfc73d50994851a5d7af9159d24ce7
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993586B2

Notizen zur Reaktion

Wird geladen…