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Potassium Carbonate → Rac-4-[3-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-methoxy-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 502436
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 502436
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18](O)[CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S([O:41][CH2:42][CH:43]2[CH2:47][O:46][C:45]([CH3:49])([CH3:48])[O:44]2)(=O)=O)=CC=1>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:41][CH2:42][CH:43]3[CH2:47][O:46][C:45]([CH3:48])([CH3:49])[O:44]3)[CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonateHCID 684587374-(3-Hydroxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 68456964Rac-4-[3-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-methoxy-benzoylamino]-piperidine-1-carboxylic acid tert-butyl esterAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1.60 g (4.6 mmol) of 4-(3-hydroxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester (example 168a) was dissolved in 50 ml of MeCN at rt; 1.29 g (9.4 mmol) of anhydrous potassium carbonate was added, followed by 1.495 g (4.8 mmol) of rac-2,2-dimethyl-1,3-dioxolan-4-yl-methyl p-toluenesulfonate. The reaction mixture was stirred at reflux for 22 hours. It was then cooled down to ambient temperature and poured into crashed ice and extracted twice with EtOAc. The organic phases were washed with water and brine, dried over MgSO4, filtered and evaporated i.V. and the residue (2.11 g) was purified by chromatography (SiO2, MeCl2/MeOH) to yield 1.52 g of the title compound as a colorless amorphous solid. MS: 465.2 (MH+).

Aufarbeitung

  1. temperatureat reflux for 22 hours
  2. additionpoured
  3. extractionextracted twice with EtOAc
  4. washThe organic phases were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated i.V
  8. customand the residue (2.11 g) was purified by chromatography (SiO2, MeCl2/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-467ae3a0b4be4af581649094ab5d79a6
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07772253B2

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