2-(1-(2-(Benzyloxy)biphenyl-3-yl)vinyl)pyridine → 3-(1-(Pyridin-2yl)ethyl)biphenyl-2-ol

HRID 45419Notes

Reaction equation

HRID 45419 reaction equation
C([O:8][C:9]1[C:14]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH2:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)C1C=CC=CC=1>[Pd].CCO.CCOC(C)=O>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:15]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:9]=1[OH:8])[CH3:16]

Participants

4

Reactant 1

HCID 582385442-(1-(2-(Benzyloxy)biphenyl-3-yl)vinyl)pyridine2×

Product 1

HCID 582385573-(1-(Pyridin-2yl)ethyl)biphenyl-2-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of 5 (0.50 g, 1.377 mmol, 1.0 equiv) and 20% Pd—C (55% H2O) (0.05 g) in 1:1 EtOH/EtOAc (30 mL) was hydrogenated at 30 psi H2 for 4.25 hr. LCMS showed some 5 remained along with A and a small amount of over-reduction products. The mixture was hydrogenated at 20 psi H2 for 2.75 hr (LCMS showed ˜2% 5 remained). The mixture was filtered through Celite, and the Celite layer was washed with 1:1 EtOH/EtOAc (30 mL). The filtrate was concentrated under reduced pressure to give a brown oil. The crude product was absorbed onto silica gel using DCM and dry-loaded on a column of silica gel (10 g) packed in hexanes. The column was eluted with hexanes (100 mL), 5% EtOAc/hexanes (100 mL) and 10% EtOAc/heptanes (200 mL). Product fractions were concentrated under reduced pressure to give 0.40 g (105%—residual solvent present) of A as a colorless, viscous oil.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe Celite layer was washed with 1:1 EtOH/EtOAc (30 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give a brown oil
  5. customThe crude product was absorbed onto silica gel
  6. washThe column was eluted with hexanes (100 mL), 5% EtOAc/hexanes (100 mL) and 10% EtOAc/heptanes (200 mL)
  7. concentrationProduct fractions were concentrated under reduced pressure
  8. customto give 0.40 g (105%—residual solvent present) of A as a colorless, viscous oil

Sources & evidence

ORD record
ord-1b1b45715ace4101acfc404571453da6
Source dataset
uspto-grants-2013_09
Patent number
US08541521B2

Reaction notes

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