Methanol → N-allyl-8,9-dihydroxy-1,2,3,11b-tetrahydrochromeno[4,3,2-de]isoquinoline

HRID 895403노트

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HRID 895403 반응식
[CH2:1]([N:4]1[CH2:13][CH:12]2[C:14]3[CH:15]=[CH:16][C:17]([O:23]C)=[C:18]([O:21]C)[C:19]=3[O:20][C:10]3[C:11]2=[C:6]([CH:7]=[CH:8][CH:9]=3)[CH2:5]1)[CH:2]=[CH2:3].B(Br)(Br)Br.CO>ClCCl>[CH2:1]([N:4]1[CH2:13][CH:12]2[C:14]3[CH:15]=[CH:16][C:17]([OH:23])=[C:18]([OH:21])[C:19]=3[O:20][C:10]3[C:11]2=[C:6]([CH:7]=[CH:8][CH:9]=3)[CH2:5]1)[CH:2]=[CH2:3]

참가 물질

5

반응물 3

HCID 887MethanolHCID 25134Boron tribromideHCID 12971923N-allyl-8,9-dimethoxy-1,2,3,11b-tetrahydrochromeno [4,3,2-de]isoquinoline

생성물 1

HCID 11779264N-allyl-8,9-dihydroxy-1,2,3,11b-tetrahydrochromeno[4,3,2-de]isoquinoline수율 119.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

N-Allyl amine 10a (0.625 g; 1.93 mmol) was dissolved in 50 ml of dichloromethane. The solution was cooled to −78° C. and 10.0 ml of BBr3 solution (1.0 M in dichloromethane) was slowly added. The solution was stirred overnight, while the reaction slowly warmed to room temperature. After recooling the solution to −78° C., 50 ml of methanol was slowly added to quench the reaction. The reaction was then concentrated to dryness. Methanol was added and the solution was concentrated. This process was repeated three times. Recystallization of the brown solid from ethanol gave 0.68 g (61%) of a white solid: mp 251-253° C. dec; 1H NMR: (300 MHz, D2O): 10.55 (s, 1H); 10.16 (s, 1H); 8.61 (t, 1H, J=9 Hz); 8.42 (d, 1H, J=9 Hz); 8.31 (d, 1H, J=9 Hz); 7.87 (d, 1H, J=9 Hz); 7.82 (d, 1H, J=9 Hz); 7.36 (q, 1H, J=9 Hz); 6.89 (m, 2H); 6.85 (d, 1H, J=15 Hz); 5.58 (m, 3H); 5.28 (m, 2H); 3.76 (d, 1H, J=3 Hz). HRCIMS m/z: Calc'd: 295.1208. Found: 295.1214.

후처리

  1. temperatureslowly warmed to room temperature
  2. customto −78° C.
  3. customto quench
  4. customthe reaction
  5. concentrationThe reaction was then concentrated to dryness
  6. additionMethanol was added
  7. concentrationthe solution was concentrated

출처 및 근거

ORD 기록
ord-3e7acaf6b84343b8b69b8e90eef2dda9
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916823B2

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