Sodium Cyanide → tert-butyl N-[(1S,3R)-3-(cyanomethyl)cyclopentyl]carbamate
Reaktionsgleichung
[C-:1]#[N:2].[K+].[C-]#N.[Na+].[C:7]([O:11][C:12]([NH:14][C@@H:15]1[CH2:19][CH2:18][C@H:17]([CH2:20]OS(C)(=O)=O)[CH2:16]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>CN(C=O)C>[C:7]([O:11][C:12](=[O:13])[NH:14][C@H:15]1[CH2:19][CH2:18][C@@H:17]([CH2:20][C:1]#[N:2])[CH2:16]1)([CH3:10])([CH3:9])[CH3:8]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
In a round-bottomed flask, methanesulfonic acid (cis)-3-tert-butoxycarbonylamino-cyclopentylmethyl ester (crude from Step 4, 779 mg) was dissolved in DMF (5 ml). Potassium cyanide (277 mg, 4.25 mmol) was added and the reaction mixture was stirred at 80° C. overnight. Sodium cyanide (104 mg, 2.12 mmol) was added and the reaction mixture was stirred at 80° C. for 48 h. The reaction was cooled to room temperature, quenched with water and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc) to afford 190 mg (38%, 2 steps) of (cis-3-cyanomethyl-cyclopentyl)-carbamic acid tert-butyl ester as a light yellow oil.
Aufarbeitung
- stirringthe reaction mixture was stirred at 80° C. for 48 h
- temperatureThe reaction was cooled to room temperature
- customquenched with water
- extractionextracted with diethyl ether (2×)
- washThe combined organic layers were washed twice with water and once with brine
- dry with materialthen dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc)
Quellen und Nachweise
- ORD-Eintrag
- ord-76c9e5024f61495c9332d39627a483d1
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08658646B2
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