Boron tribromide → HCID 44608136, 화합물

HRID 2427779노트

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HRID 2427779 반응식
C[O:2][C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[CH:11]1[N:16]([CH3:17])[CH2:15][CH2:14][C:13]([CH3:18])=[CH:12]1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:17][N:16]1[CH2:15][CH2:14][C:13]([CH3:18])=[CH:12][CH:11]1[C:4]1[CH:5]=[CH:6][C:7]([OH:9])=[CH:8][C:3]=1[OH:2]

참가 물질

5

반응물 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 44610348HCID 44610348, 화합물

생성물 1

HCID 44608136HCID 44608136, 화합물수율 35%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 6-(2,4-dimethoxyphenyl)-1,4-dimethyl-1,2,3,6-tetrahydro-pyridine (6) (300 mg, 1.27 mmol) in dichloromethane (20 ml) cooled at 0° C. under nitrogen was added boron tribromide (3.1 ml, 3.18 mmol of 1.0M solution in dichloromethane), the resultant dark solution was allowed to warm to room temperature and stirred for 1 hour. The solution was poured onto ice and basified with sodium bicarbonate. The layers were separated and the aqueous layer was extracted with dichloromethane (20 ml), the combined organic layers were dried over anhydrous magnesium sulphate, filtered and evaporated to a gum (200 mg). The material was purified on a 10 g silica cartridge eluting with methanol/dichloromethane/ammonia (7:92:1) to yield 4-(1,4-dimethyl-1,2,5,6-tetrahydropyridin-2-yl)-benzene-1,3-diol (8) (93 mg, 35%) as a gum, 1H NMR D6-acetone ??1.67 (s, 3H), 1.97 (m,1H), 2.3 (s, 3H), 2.42 (m, 1H), 2.74 (m, 1H), 3.08 (m, 1H), 3.74 (s, 1H), 5.15 (s, 1H), 6.2 (d, 1H J=2), 6.27 (dd, 1H J=2.8), 6.82 (d, 1H J=8), 9.4 (bs, 2H).

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (20 ml)
  3. dry with materialthe combined organic layers were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to a gum (200 mg)
  6. customThe material was purified on a 10 g silica cartridge
  7. washeluting with methanol/dichloromethane/ammonia (7:92:1)

출처 및 근거

ORD 기록
ord-73fa6a9c187a42b4acfce6208367d589
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968711B2

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