Boron tribromide → HCID 44608136、化合物

HRID 1432516ノート

反応式

HRID 1432516 の反応式
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]

参加物

5

反応物 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 44610348HCID 44610348、化合物

生成物 1

HCID 44608136HCID 44608136、化合物収率 35%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-580c7d1d9175467ca325665d1292b79b
出典データセット
uspto-grants-2009_11
特許番号
US07612101B2

反応ノート

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