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

HRID 1359150Notes

Reaction equation

HRID 1359150 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]3[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][C:8]=3[CH:9]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:15][CH:14]=3)[O:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]3[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][C:8]=3[CH:9]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:17][CH:18]=3)[O:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 11396956(+)-1-[3-Methoxy-6-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-6h-benzo[c]chromen-8-yl]-ethanone

Product 1

HCID 11374158(+)-1-[3-Hydroxy-6-[4-(2-piperidin-1-yl-ethoxy)phenyl]-6h-benzo[c]chromen-8-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

The mixture containing the compound from Step H (0.25 g, 0.565 mmol) was dissolved in CH2Cl2 (40 ml) and cooled to −78° C. and BBr3 in CH2Cl2 (1M, 11 ml) was added. The mixture was kept at −78° C. and allowed to warm to 15° C. overnight. The reaction was quenched with saturated NaHCO3 (5 ml) and extracted with CH2Cl2 (20 ml). The organic layer was washed with saturated NaHCO3, water and dried over Na2SO4. The solvent was removed and the crude product purified by preparative TLC plates. 1H-NMR (400 MHz, CDCl3) δH 1.55 (2H, m, NCH2CH2CH2), 1.80 (4H, m, NCH2CH2CH2), 2.56 (3H, s, COCH3), 2.81 (4H, m, NCH2CH2CH2), 3.01 (2H, m, NCH2CH2O), 4.22 (2H, m, NCH2CH2O), 6.13 (1H, s, Ph2CHO), 6.50 (1H, s, ArH), 6.60 (1H, d, ArH), 6.80 (2H, d, ArH), 7.21 (2H, d, ArH), 7.49 (1H, s, ArH), 7.65 (1H, d, ArH), 7.74 (1H, d, ArH), 7.97 (1H, d, ArH).

Workup

  1. customwas kept at −78° C.
  2. temperatureto warm to 15° C. overnight
  3. customThe reaction was quenched with saturated NaHCO3 (5 ml)
  4. extractionextracted with CH2Cl2 (20 ml)
  5. washThe organic layer was washed with saturated NaHCO3, water
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed
  8. customthe crude product purified by preparative TLC plates

Sources & evidence

ORD record
ord-11ba6bdd36c2467cb93ecc0d380c0e4d
Source dataset
uspto-grants-2003_07
Patent number
US06599921B2

Reaction notes

Loading…