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Ammonia → (2R,4R)-1-tert-butyl 2-methyl 4-(3-(4-cyanophenyl)ureido)piperidine-1,2-dicarboxylate

HRID 1685475
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1685475
[N:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)=[C:2]=[O:3].[NH2:12][C@@H:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:15]([C:26]([O:28][CH3:29])=[O:27])[CH2:14]1.CCN(CC)CC.N>C1COCC1.CO>[C:8]([C:7]1[CH:10]=[CH:11][C:4]([NH:1][C:2](=[O:3])[NH:12][C@@H:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C@@H:15]([C:26]([O:28][CH3:29])=[O:27])[CH2:14]2)=[CH:5][CH:6]=1)#[N:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 1703804-Cyanophenyl isocyanateHCID 54209755(2R,4R)-1-tert-butyl 2-methyl 4-aminopiperidine-1,2-dicarboxylate

Produkt 1

HCID 57539094(2R,4R)-1-tert-butyl 2-methyl 4-(3-(4-cyanophenyl)ureido)piperidine-1,2-dicarboxylateAusbeute 93,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-isocyanatobenzonitrile (1.17 g, 8.13 mmol) was added to a solution of (2R,4R)-1-tert-butyl 2-methyl 4-aminopiperidine-1,2-dicarboxylate (2.0 g, 7.7 mmol) and NEt3 (1.3 mL, 9.3 mmol) in THF (30 mL), and the resulting solution was stirred at room temperature for 6 hours. 1M ammonia in methanol (5 mL) was then added to the reaction mixture to quench excess isocyanine. Water (100 mL) and ethyl acetate (200 mL) were added to the mixture. The organic layer was separated and dried over MgSO4 and concentrated to give a solid. Purification by Companion (ReadySep, 80 g, silica gel packed) using ethyl acetate/heptane from 40-70% as eluent provided the title compound as a white solid 2.9 g (90%). LC-MS: 403.2, 401.3 (t=2.6 min).

Aufarbeitung

  1. customto quench excess isocyanine
  2. additionWater (100 mL) and ethyl acetate (200 mL) were added to the mixture
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a solid
  7. customPurification by Companion (ReadySep, 80 g, silica gel packed)

Quellen und Nachweise

ORD-Eintrag
ord-e3a1961d82b44dceae1a7b39a4a6341b
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08148401B2

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