Cesium carbonate → Tert-butyl 3-(2-fluorophenoxy)cyclohexylcarbamate
Reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1I.CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu](I)I>[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
A reaction mixture of tert-butyl 3-hydroxycyclohexylcarbamate (4 mmol, 861 mg), 1-fluoro-2-iodobenzene (5 mmol, 585 4), copper iodide (0.4 mmol, 76 mg), 3,4,7,8-tetramethyl-1,10-phenanthroline (0.8 mmol, 190 mg) and cesium carbonate (10 mmol, 3.26 g) in toluene (5 mL) was stirred at 110° C. for overnight under argon. The reaction mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated. The mixture was purified by silica gel column chromatography. The product, tert-butyl 3-(2-fluorophenoxy)cyclohexylcarbamate, was eluted off the column using 15% EtOAc in Hexane.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered through celite
- concentrationThe filtrate was concentrated
- customThe mixture was purified by silica gel column chromatography
- washThe product, tert-butyl 3-(2-fluorophenoxy)cyclohexylcarbamate, was eluted off the column
Sources & evidence
- ORD record
- ord-de94344fee0c49f68e3aaabeaac80058
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09351965B2
Reaction notes
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