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

HRID 344827ノート

反応式

HRID 344827 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dc95b1de18ec42a1bc62220a212b868c
出典データセット
uspto-grants-1991_10
特許番号
US05053525

反応ノート

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