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Triethylamine → tert-Butyl 4-[2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazol-4-yl]piperidine-1-carboxylate

HRID 716712
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 716712
Br[CH2:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=O.[O:18]1[CH2:23][CH2:22][CH:21]([C:24]([NH2:26])=[O:25])[CH2:20][CH2:19]1.CCN(CC)CC.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>CN1C(=O)N(C)CCC1.O.ClCCl>[O:18]1[CH2:23][CH2:22][CH:21]([C:24]2[O:25][CH:2]=[C:3]([CH:5]3[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]3)[N:26]=2)[CH2:20][CH2:19]1
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Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 13197203Oxane-4-carboxamideHCID 18187487tert-Butyl 4-(2-Bromoacetyl)piperidine-1-carboxylate

Produkt 1

HCID 70171103tert-Butyl 4-[2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazol-4-yl]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Lösungsmittel

Versuchsvorschrift

tert-Butyl 4-(bromoacetyl)piperidine-1-carboxylate (1.07 g, 3.49 mmol) and tetrahydro-2H-pyran-4-carboxamide (0.95 g, 7.36 mmol) were mixed heated in DMPU (6.99 mL) at 150° C. for 4 hrs. LC-MS indicated that the reaction was completed and the product showed loss of Boc group. Et3N (1.46 mL, 10.5 mol) and Boc2O (0.915 g, 4.19 mmol) were added and the mixture was stirred at RT for 30 min. The reaction was diluted with water and dichloromethane. The two layers were separated and the organic layer was extracted with dichloromethane. The combined organic layers were washed with H2O (twice) and brine, dried over Na2SO4, filtered and conc. The crude (still containing DMPU) was used without purification. LC-MS: [M+H]+=337.4.

Aufarbeitung

  1. customThe two layers were separated
  2. extractionthe organic layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with H2O (twice) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customconc. The crude (still containing DMPU) was used without purification

Quellen und Nachweise

ORD-Eintrag
ord-59ee269021374425940789826f7f61ca
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09193697B2

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