HCID 59808495, compound → HCID 40419069, compound

HRID 1942510Notes

Reaction equation

HRID 1942510 reaction equation
[OH:1][C@H:2]1[C@:7](O)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1>C(O)C.[Ni]>[OH:1][C@H:2]1[C@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1

Participants

4

Reactant 1

HCID 59808495HCID 59808495, compound

Product 1

HCID 40419069HCID 40419069, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl (3R,4R)-3,4-dihydroxy-4-phenylpiperidine-1-carboxylate (120 g) in ethanol (4.3 L) was added Raney nickel (240 g), and the mixture was refluxed for 48 hours with bubbling of hydrogen gas. The reaction solution was cooled, and filtered on celite, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give the title compound (105.1 g, 99.4% ee).

Workup

  1. temperaturethe mixture was refluxed for 48 hours
  2. customwith bubbling of hydrogen gas
  3. temperatureThe reaction solution was cooled
  4. filtrationfiltered on celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-31898958666a4c6e83547c3fa2e83497
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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