Boron trifluoride etherate → (+)-1-[3-Methoxy-6-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-6h-benzo[c]chromen-8-yl]-ethanone

HRID 1359149ノート

反応式

HRID 1359149 の反応式
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[CH:27][C:7]=3[CH:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:14][CH:13]=3)[O:9]2)=[CH:4][CH:3]=1.[SiH](CC)(CC)[CH2:35]C.B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:35][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[CH:27][C:7]=3[CH:8]([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:16][CH:17]=3)[O:9]2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 11374158(+)-1-[3-Hydroxy-6-[4-(2-piperidin-1-yl-ethoxy)phenyl]-6h-benzo[c]chromen-8-yl]-ethanone

生成物 1

HCID 11396956(+)-1-[3-Methoxy-6-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-6h-benzo[c]chromen-8-yl]-ethanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

The compound from Step G (1.66 g, 3.2 mmol) was dissolved in CH2Cl2 (90 mL) and cooled to −78° C. Et3SiH (3.1 ml, 19.2 mmol) and BF3-Et2O (2.6 ml, 19.2 mmol) were added slowly under Ar. The mixture was stirred at −78° C., then at room temperature overnight. Saturated NaHCO3 (100 ml) was added and the mixture extracted three times with ethyl acetate (150 ml). The combined organic layer was washed with brine (100 ml) and dried over MgSO4. The solvent was removed and the crude product was chromatographed on silica gel with 7% CH3OH/CH2Cl2 to yield a fraction containing a mixture of the title compound along with side products and a fraction containing 0.52 g (32%) of the title compound. 1H-NMR (400 MHz, CDCl3) δH 1.42 (2H, m, NCH2CH2CH2), 1.59 (4H, m, NCH2CH2CH2), 2.50 (7H, m, NCH2CH2CH2 and COCH3), 2.76 (2H, m, NCH2CH2O), 3.77 (3H, s, OCH3), 4.08 (2H, m, NCH2CH2O), 6.14 (1H, s, Ph2CHO), 6.50 (1H, s, ArH), 6.61 (1H, d, ArH), 6.86 (2H, d, ArH), 7.22 (2H, d, ArH), 7.45 (1H, s, ArH), 7.66 (1H, d, ArH), 7.72 (1H, d, ArH), 7.93 (1H, d, ArH).

後処理

  1. customat room temperature
  2. customovernight
  3. extractionthe mixture extracted three times with ethyl acetate (150 ml)
  4. washThe combined organic layer was washed with brine (100 ml)
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed
  7. customthe crude product was chromatographed on silica gel with 7% CH3OH/CH2Cl2
  8. customto yield a fraction
  9. additioncontaining

出典と根拠

ORDレコード
ord-19812577e47c4c45bee3edd1e4b7218c
出典データセット
uspto-grants-2003_07
特許番号
US06599921B2

反応ノート

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