Triphenylphosphine → (R)-2-[2-(2,5-difluorophenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione

HRID 1271459ノート

反応式

HRID 1271459 の反応式
[OH:1][CH2:2][C@H:3]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=1O.CCOC(/N=N/C(OCC)=O)=O>>[F:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=1[O:1][CH2:2][C@H:3]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH3:4]

参加物

5

反応物 4

HCID 11776TriphenylphosphineHCID 949522,5-DifluorophenolHCID 6418462-[(2R)-1-hydroxypropan-2-yl]-2,3-dihydro-1H-isoindole-1,3-dioneHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 69472648(R)-2-[2-(2,5-difluorophenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione収率 63.9%

実験手順

A solution of 15.8 g (77 mmol) of (R)-2-(2-hydroxy-1-methylethyl)-1H-isoindole-1,3(2H)-dione, 24.2 g (92 mmol) of triphenylphosphine and 10.0 g (77 mmol) of 2,5-difluorophenol was stirred while 18.2 mL (116 mmol) of diethylazodicarboxylate was added dropwise. After stirring at ambient temperature overnight, solvent was removed and the residue was dissolved in ethyl acetate. The ethyl acetate was washed with water and brine. Drying (MgSO4) and removal of solvent gave an oil which was chromatographed on silica gel to give 15.6 g of the title compound of Step C as an oil, 1H NMR (CDCl3) δ 1.55 (d, 3H), 4.25 (m, 1H), 4.8 (m, 1H), 6.55 (m, 1H), 6.65 (m, 1H), 6.9 (m, 1H), 7.7 (m, 2H), 7.85 (m, 2H).

後処理

  1. additionwas added dropwise
  2. customsolvent was removed
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe ethyl acetate was washed with water and brine
  5. customDrying
  6. custom(MgSO4) and removal of solvent
  7. customgave an oil which
  8. customwas chromatographed on silica gel

出典と根拠

ORDレコード
ord-dc233027ce5c4875960304ff63aa28a8
出典データセット
uspto-grants-2007_04
特許番号
US07205331B2

反応ノート

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