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

HRID 1359149Notes

Reaction equation

HRID 1359149 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-19812577e47c4c45bee3edd1e4b7218c
Source dataset
uspto-grants-2003_07
Patent number
US06599921B2

Reaction notes

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