Hexane → HCID 58495810, compound
Reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4]1.[F:19][C:20]([F:28])(S(F)(=O)=O)C(O)=O.CCCCCC.N.CO>C(#N)C.[Cu](I)I.C(OCC)(=O)C>[F:19][CH:20]([F:28])[O:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:4]1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate (2.49 g, 10.0 mmol) was dissolved in acetonitrile (100 mL), to which copper iodide (I) (2.86 g, 15.0 mmol) and 2,2-difluoro-2-(fluorosulfonyl)acetic acid (2.66 g, 15.0 mmol) were added, followed by stirring at 80° C. for 20 minutes. The mixture was brought down to room temperature, to which adequate amounts of hexane and ethyl acetate were added, followed by neutralization with a 2M ammonia/methanol solution. Impurities were filtered off, and the solvent was distilled off under reduced pressure. The residue thus obtained was purified by basic silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, V/V) to give the desired title compound (1.82 g, yield 61%).
Workup
- additionwere added
- additionwere added
- filtrationImpurities were filtered off
- distillationthe solvent was distilled off under reduced pressure
- customThe residue thus obtained
- customwas purified by basic silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, V/V)
Sources & evidence
- ORD record
- ord-b2bf19e2c4fb446281673320570400d1
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08685981B2
Reaction notes
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