Lawesson's reagent → tert-Butyl 4-carbamothioylpiperidine-1-carboxylate

HRID 1497644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497644
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COCCOC.CC1OC(C=CC2C=C3CCCN4CCCC(=C34)C=2)=CC(=C(C#N)C#N)C=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:59])=CC=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[S:59])[NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 87949Lawesson's reagentHCID 27356461-(tert-Butoxycarbonyl)piperidine-4-carboxamideHCID 131734219Dme dcm 2

Produkt 1

HCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateAusbeute 186,7 %

Versuchsvorschrift

To a solution of tert-butyl-4-carbamoylpiperidine-1-carboxylate (2.65 g, 11.62 mmol) in a DME/DCM 2:1 mixture (78 mL), Lawesson reagent (2.35 g, 5.81 mmol, 0.5 eq) was added and the mixture was stirred at r.t. overnight. The solvent was removed and the residue was taken up with ethyl acetate and washed with saturated aqueous K2CO3. The organic layer was separated, dried over Na2SO4 and concentrated to dryness. The residue was triturated with diethyl ether and dried to give 2.65 g (92%) of the title compound as a white solid.

Aufarbeitung

  1. customThe solvent was removed
  2. washwashed with saturated aqueous K2CO3
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was triturated with diethyl ether
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7d1e98ba6f04467fb6374ff3c4a35cc8
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199979B2

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