1,10-Phenanthroline → HCID 86609638, compound

HRID 1162026Notes

Reaction equation

HRID 1162026 reaction equation
I[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[F:14][CH:15]1[CH:20]([OH:21])[CH2:19][CH2:18][N:17]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:16]1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu]I>[F:14][C@H:15]1[C@H:20]([O:21][C:2]2[C:10]3[O:9][CH:8]=[CH:7][C:6]=3[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=2)[CH2:19][CH2:18][N:17]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:16]1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 21864764HCID 21864764, compoundHCID 42609254Tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 86609638HCID 86609638, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Procedure

7-Iodo-5-nitrobenzofuran (2.0 g, 6.9 mmol), tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate* (3.8 g, 17.3 mmol; mixture of cis/trans isomers), 1,10-phenanthroline (0.50 g, 2.8 mmol), CuI (0.26 g, 1.4 mmol) and Cs2CO3 (4.5 g, 13.8 mmol) were heated in toluene (20 mL) at 120° C. for 72 h. The reaction mixture was filtered through Celite and evaporated. The resulting diastereomers were separated by flash chromatography using heptane/EtOAc [(4:1)→(2:1)] to yield 255 mg of the cis-isomer and 919 mg of the trans-isomer. *Prepared according to the procedure described in WO2001085728.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customevaporated
  3. customThe resulting diastereomers were separated by flash chromatography
  4. customto yield 255 mg of the cis-isomer and 919 mg of the trans-isomer

Sources & evidence

ORD record
ord-a7f61fb6264740fcb836a183905b81c0
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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