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Sodium Bicarbonate → 3,5-Dichlorobenzyl 4-(((tert-butoxycarbonyl)amino)methyl)-2-methylpiperidine-1-carboxylate

HRID 1480370
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1480370
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH:11]([CH3:15])[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[C:17](Cl)(=[O:28])[O:18][CH2:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:17]([O:18][CH2:19][C:20]2[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=2)=[O:28])[CH:11]([CH3:15])[CH2:10]1)=[O:16])([CH3:4])([CH3:2])[CH3:3]
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Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 133055323,5-Dichlorobenzyl ChloroformateHCID 83918261tert-Butyl N-[(2-methylpiperidin-4-yl)methyl]carbamate

Produkt 1

HCID 867226283,5-Dichlorobenzyl 4-(((tert-butoxycarbonyl)amino)methyl)-2-methylpiperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

A mixture comprising tert-butyl((2-methylpiperidin-4-yl)methyl)carbamate (step 2) (1.15 g, 5.04 mmol) and 3,5-dichlorobenzyl carbonochloridate (1.327 g, 5.54 mmol) in DCM (15 ml) was treated with aq. saturated sodium bicarbonate (0.504 ml, 5.04 mmol) and stirred at room temperature for 18 hours. The organic portion was separated and the aqueous phase extracted with DCM (2×10 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. Further purification by chromatography on silica, eluting in 0-20% 2M ammonia in MeOH in DCM afforded the title compound;

Aufarbeitung

  1. customThe organic portion was separated
  2. extractionthe aqueous phase extracted with DCM (2×10 ml)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customFurther purification by chromatography on silica
  7. washeluting in 0-20% 2M ammonia in MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-667d50e1f7f34a12b37e7adc8606d690
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09409895B2

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