Sodium Azide → tert-butyl [(1R,2R)-2-azido-3,3-difluorocyclohexyl]carbamate
Reaktionsgleichung
FC(F)(F)S(O[C@H:7]1[C@H:12]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH2:10][CH2:9][C:8]1([F:22])[F:21])(=O)=O.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[N:25]([C@H:7]1[C:8]([F:22])([F:21])[CH2:9][CH2:10][CH2:11][C@H:12]1[NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N+:26]=[N-:27]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A solution of (1S,6R)-6-[(tert-butoxycarbonyl)amino]-2,2-difluorocyclohexyl trifluoromethanesulfonate 34 (2.32 g, 6.05 mmol) and sodium azide (2.36 g, 36.3 mmol) in DMF was sealed and heated to 100° C. for 3 hours in a microwave reactor. The reaction was partitioned between water and ethyl acetate. The organics were washed with water, dried over magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (0-15% ethyl acetate in hexanes) gave 0.94 g (56%) of tert-butyl [(1R,2R)-2-azido-3,3-difluorocyclohexyl]carbamate 36 as a white solid: NMR (500 MHz, CDCl3) δ 4.75 (1H, m), 3.98 (1H, bs), 3.88 (1H, bm), 1.96 (2H, m), 1.70 (2H, m), 1.46 (9H, s), 1.37 (2H, m).
Aufarbeitung
- customThe reaction was partitioned between water and ethyl acetate
- washThe organics were washed with water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated in vacuo
- customPurification by flash chromatography (0-15% ethyl acetate in hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-dcc1faaa11f549dc966c8fa3e9c39f15
- Quelldatensatz
- uspto-grants-2013_06
- Patentnummer
- US08461162B2
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