Reaktion #427356

ord-42cf12d29d7846d3afb2f86be8018863

Reaktionsgleichung

C[C@H]1NC(=O)[C@@H](NC(=O)OC(C)(C)C)C[C@H]1c1ccccc1
tert-butyl[(3S,5S,6R)-6-methyl-2-oxo-5-phenylpiperidin-3-yl]carbamate
COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1
Lawesson's Reagent
→
C[C@H]1NC(=S)[C@@H](NC(=O)OC(C)(C)C)C[C@H]1c1ccccc1
title compound
Ausbeute 170.1%
C[C@H]1NC(=S)[C@@H](NC(=O)OC(C)(C)C)C[C@H]1c1ccccc1
tert-Butyl[(3S,5S,6R)-6-methyl-5-phenyl-2-thioxopiperidin-3-yl]carbamate
Ausbeute 170.1%

Edukte

C[C@H]1NC(=O)[C@@H](NC(=O)OC(C)(C)C)C[C@H]1c1ccccc1
tert-butyl[(3S,5S,6R)-6-methyl-2-oxo-5-phenylpiperidin-3-yl]carbamate
COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1
Lawesson's Reagent

Reagenzien

Keine

Lösungsmittel

Cc1ccccc1
toluene

Reaktionsbedingungen

Temperatur
40°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstige16 h
  2. 2
    TemperaturThe mixture was cooled to ambient temperature
  3. 3
    Einengenconcentrated
  4. 4
    SonstigePurification by silica gel chromatography (100% hexanes→60% hexanes/ethyl acetate)

Vorschrift

To a solution of tert-butyl[(3S,5S,6R)-6-methyl-2-oxo-5-phenylpiperidin-3-yl]carbamate (796 mg, 2.62 mmol) in toluene (26.2 mL) was added Lawesson's Reagent (539 mg, 1.33 mmol) and the resulting mixture stirred at 40° C. 16 h. The mixture was cooled to ambient temperature and concentrated. Purification by silica gel chromatography (100% hexanes→60% hexanes/ethyl acetate) gave the title compound (725 mg). MS 343.3 (M+Na).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08895572B2uspto-grants-2014_11