Boric Acid → Methyl 7-(4'-fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl)-3-hydroxy-5-oxoheptanoate

HRID 344827Notes

Reaction equation

HRID 344827 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2[CH2:16][CH2:17][C:18]2[CH2:22][CH:21]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[O:20]N=2)=[CH:4][C:3]=1[CH3:28].B(O)(O)[OH:30]>[Pd].CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2[CH2:16][CH2:17][C:18](=[O:30])[CH2:22][CH:21]([OH:20])[CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:4][C:3]=1[CH3:28]

Participants

6

Reactant 2

HCID 7628Boric AcidHCID 54381644Methyl 3-[2-(4'-fluoro-3,3',5-trimethyl[1,1'-biphenyl]-2-yl)ethyl]-4,5-dihydro-5-isoxazoleacetate

Product 1

HCID 67947384Methyl 7-(4'-fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl)-3-hydroxy-5-oxoheptanoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 0.1 g (0.26 mmol) of the isoxazoline from Step E, 50 mg of 10% palladium on carbon catalyst and 48 mg (0.78 mmol) of boric acid in 3 ml of methanol and 0.3 ml of water was stirred under hydrogen (1 atmosphere) at room temperature for 2.5 hours. The mixture was filtered and the filtrate was poured into brine and extracted with ether. The ethereal extract was washed with 5% (w/v) aqueous sodium bicarbonate solution, dried (MgS04), filtered and evaporated to dryness to give 92 mg (0.23 mmol, 89%) as a pale yellow oil. nmr (CDCl3) δ: 2.30 (6H, a methyl singlet and a methyl doublet), 2.33 (3H, s), 2.35-2.5 (6H, m), 2.75-2.85 (2H, m), 3.30 (H, d), 3.70 (3H, s), 4.37 (H, m), 6.83 (H, bs), 6.95-7.1 (4H, m). IR (neat) 3450, 1710 cm-1.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was poured into brine
  3. extractionextracted with ether
  4. extractionThe ethereal extract
  5. washwas washed with 5% (w/v) aqueous sodium bicarbonate solution
  6. customdried (MgS04)
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customto give 92 mg (0.23 mmol, 89%) as a pale yellow oil

Sources & evidence

ORD record
ord-dc95b1de18ec42a1bc62220a212b868c
Source dataset
uspto-grants-1991_10
Patent number
US05053525

Reaction notes

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