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

HRID 1359150노트

반응식

HRID 1359150 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-11ba6bdd36c2467cb93ecc0d380c0e4d
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599921B2

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