1,1'-Carbonyldiimidazole → Tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylpiperidine-1-carboxylate

HRID 1809582

Reaktionsgleichung

Reaktionsgleichung von HRID 1809582
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH:10]([CH3:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1(C(N2C=CN=C2)=O)C=CN=C1.Cl.[CH3:31][O:32][NH:33][CH3:34]>C(Cl)Cl>[CH3:31][O:32][N:33]([CH3:34])[C:14]([CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH:10]1[CH3:17])=[O:16]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 4248616N-Boc-3-methyl-4-piperidinecarboxylic acid

Produkt 1

HCID 86601647Tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylpiperidine-1-carboxylateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(tert-butoxycarbonyl)-3-methylpiperidine-4-carboxylic acid (3.00 g, 12.3 mmol) in CH2Cl2 (200 mL) was added di(1H-imidazol-1-yl)methanone (2.19 g, 13.6 mmol) portionwise. After the bubbling ceased (˜60 minutes), N-methoxymethanamine hydrochloride (1.32 g, 13.6 mmol) was added in one portion. The mixture was stirred overnight at ambient temperature, then washed with water, 1N HCl, and saturated sodium bicarbonate. The organic layer was dried, filtered, and concentrated to give the desired product (2.29 g, 64.8% yield) as a colorless oil.

Aufarbeitung

  1. additionwas added in one portion
  2. washwashed with water, 1N HCl, and saturated sodium bicarbonate
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-492e85ed25814570945e00d1c74e3766
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362037B2

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