Triethylamine → 1,1-Dimethylethyl (1-trifluoromethanesulphonylpiperidin-4-yl)carbamate

HRID 1256221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256221
[CH3:1][C:2]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])[CH3:3].C(N(CC)CC)C.[F:22][C:23]([F:29])([F:28])[S:24](Cl)(=[O:26])=[O:25].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:22][C:23]([F:29])([F:28])[S:24]([N:12]1[CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:14][CH2:13]1)(=[O:26])=[O:25]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidine

Produkt 1

HCID 866649281,1-Dimethylethyl (1-trifluoromethanesulphonylpiperidin-4-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 150 ml round-bottomed flask equipped with a magnetic stirrer is charged under argon with 2 g of 4-N-boc-aminopiperidine in 35 ml of DCM, 82 mg of 4-dimethylaminopyridine (DMAP) and 1.86 ml of triethylamine. After cooling to 0° C. using an ice bath, 1.6 ml of trifluoromethanesulphonyl chloride are added dropwise. The mixture is stirred at 0° C. for 30 min and then at RT for 1 h. It is poured into 100 ml of saturated aqueous sodium bicarbonate solution. It is extracted with AcOEt, washed with saturated aqueous NaCl solution, dried over MgSO4, filtered and concentrated to dryness under RP. Chromatography on silica gel (15-40 μm), eluting with a mixture of DCM and methanol (98/02 by vol.), gives 1.5 g of 1,1-dimethylethyl (1-trifluoromethanesulphonylpiperidin-4-yl)carbamate (cream solid). MS (E/I): m/z=232 (M+).

Aufarbeitung

  1. customA 150 ml round-bottomed flask equipped with a magnetic stirrer
  2. waitat RT for 1 h
  3. extractionIt is extracted with AcOEt
  4. washwashed with saturated aqueous NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under RP
  8. washChromatography on silica gel (15-40 μm), eluting with a mixture of DCM and methanol (98/02 by vol.)

Quellen und Nachweise

ORD-Eintrag
ord-55bd18416942432db94e68621e464505
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461175B2

Notizen zur Reaktion

Wird geladen…