HCID 67073443, compound → HCID 67073121, compound

HRID 2253028Notes

Reaction equation

HRID 2253028 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH:14]([C:16]2[CH:21]=[C:20]([F:22])[C:19]([O:23]CC3C=CC=CC=3)=[CH:18][C:17]=2[F:31])Br)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:16]2[CH:21]=[C:20]([F:22])[C:19]([OH:23])=[CH:18][C:17]=2[F:31])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67073443HCID 67073443, compound

Product 1

HCID 67073121HCID 67073121, compoundYield 16.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of palladium on carbon (10%, 0.47 g) in a solution of 4.7 g of (S)-2-[(4-benzyloxy-2,5-difluoro-phenyl)-bromo-methyl]-morpholine-4-carboxylic acid tert-butyl ester in ethanol (400 ml) was hydrogenated at room temperature and normal pressure till the theoretical amount of hydrogen had been consumed. Solids were removed by filtration and the filtrate was concentrated in vacuo. The residue was partitioned with ethyl acetate and saturated sodium bicarbonate solution. Organic phases were pooled, washed with brine and dried with Na2SO4 before being concentrated in vacuo. The residue was then purified by column chromatography (dichloromethane-diethyl ether (19:1)/silica gel) to give 0.5 g of the title compound.

Workup

  1. customwas hydrogenated at room temperature
  2. customnormal pressure till the theoretical amount of hydrogen had been consumed
  3. customSolids were removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was partitioned with ethyl acetate and saturated sodium bicarbonate solution
  6. washwashed with brine
  7. dry with materialdried with Na2SO4
  8. concentrationbefore being concentrated in vacuo
  9. customThe residue was then purified by column chromatography (dichloromethane-diethyl ether (19:1)/silica gel)

Sources & evidence

ORD record
ord-37439f7f677440e89ae4839f15f9cb56
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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