HCID 67542955, compound → HCID 67543036, compound

HRID 2354960Notes

Reaction equation

HRID 2354960 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C@@:9]([C:13]2[CH:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:16]=[CH:17][CH:18]=2)(O)[C@@H:8]([OH:25])[CH2:7]1)=[O:5])[CH3:2]>CCO.[Ni]>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C@H:9]([C:13]2[CH:14]=[C:15]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:16]=[CH:17][CH:18]=2)[C@@H:8]([OH:25])[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 67542955HCID 67542955, compound

Product 1

HCID 67543036HCID 67543036, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a vigorously stirred solution of the title B compound, (3S,4S)-4-biphenyl-3-yl-3,4-dihydroxy-piperidine-1-carboxylic acid ethyl ester (4.2 g, 12.05 mmol) in EtOH (250 mL) is added 6.5 g Raney-Nickel. The stirred suspension is heated to reflux for 4 h, then allowed to cool to room temperature, filtered over a celite pad and rinsed with EtOH. The solvent is removed under reduced pressure and purification by flash column chromatography (hexane/EtOAc 4/1 to 1/2) affords the desired product: (3R,4R)-4-Biphenyl-3-yl-3-hydroxy-piperidine-1-carboxylic acid ethyl ester. TLC, Rf (Hexane/EtOAc 2/1)=0.65. MS 326.1 [M+H]. Rt (HPLC, Nucleosil C18, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 5.62 min.

Workup

  1. temperatureThe stirred suspension is heated
  2. temperatureto reflux for 4 h
  3. filtrationfiltered over a celite pad
  4. washrinsed with EtOH
  5. customThe solvent is removed under reduced pressure and purification by flash column chromatography (hexane/EtOAc 4/1 to 1/2)

Sources & evidence

ORD record
ord-7ccfeb15a06c4e1d9ba0c53fef50743d
Source dataset
uspto-grants-2010_07
Patent number
US07754727B2

Reaction notes

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