Triethylamine → Benzyl 4-((methanesulfonyl)oxy)piperidine-1-carboxylate

HRID 1518462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518462
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:25][S:26]([O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1)(=[O:28])=[O:27]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Produkt 1

HCID 58303455Benzyl 4-((methanesulfonyl)oxy)piperidine-1-carboxylateAusbeute 107,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To benzyl 4-hydroxypiperidine-1-carboxylate (48.8 g, 207 mmol) in CH2Cl2 (400 mL) was added triethylamine (57.8 mL, 415 mmol), the mixture was cooled to 0° C. under nitrogen and then methanesulfonyl chloride (17.78 mL, 228 mmol) was added over 15 minutes keeping internal temperature below 30° C. After 2 hours at 0° C., the reaction was quenched with 300 mL of 0.1 N aqueous HCl, the organic layer was washed with 300 mL of water, 300 mL of brine, dried with MgSO4, filtered and concentrated to give the product (69.5 g) as an amber liquid which was used without further purification. MS (ESI) 314.4 (M+1).

Aufarbeitung

  1. customtemperature below 30° C
  2. customthe reaction was quenched with 300 mL of 0.1 N aqueous HCl
  3. washthe organic layer was washed with 300 mL of water, 300 mL of brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b98d55d6b0df473aaa2c4b2822b6b2bd
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232404B2

Notizen zur Reaktion

Wird geladen…