Methanol → [1R,3S] 1-Aminomethyl-5-hydroxy-3-phenyl-1,2,3,4-tetrahydronaphthalene formic acid salt

HRID 982096ノート

反応式

HRID 982096 の反応式
Cl.[NH2:2][CH2:3][C@H:4]1[C:13]2[C:8](=[C:9]([O:14][CH3:15])[CH:10]=[CH:11][CH:12]=2)[CH2:7][C@@H:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5]1.B(Br)(Br)Br.C[OH:27]>C(Cl)Cl>[CH:15]([OH:14])=[O:27].[NH2:2][CH2:3][C@H:4]1[C:13]2[C:8](=[C:9]([OH:14])[CH:10]=[CH:11][CH:12]=2)[CH2:7][C@@H:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5]1

参加物

5

反応物 3

HCID 887MethanolHCID 25134Boron tribromideHCID 67931190[1R,3S] 1-aminomethyl-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene hydrochloride

生成物 1

HCID 67931390[1R,3S] 1-Aminomethyl-5-hydroxy-3-phenyl-1,2,3,4-tetrahydronaphthalene formic acid salt収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

[1R,3S] 1-Aminomethyl-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene hydrochloride (0.16 g, 0.53 mmol), from Step 1, was suspended in 5 mL of methylene chloride and the suspension was cooled to -78° C. in a dry ice/acetone bath. Boron tribromide (19 mL of a 1 M solution in methylene chloride, 19 mmol) was added and the reaction mixture was allowed to warm to ambient temperature, kept at ambient temperature for 1.5 h then cooled to -78° C. Methanol (3 mL) was added to the reaction mixture and it was again allowed to warm to ambient temperature then concentrated in vacuo. The residue was dissolved in methanol and reconcentrated. The residue was redissolved in methanol and the methanol solution was chromatographed on a silica gel column eluted with ethyl acetate:formic acid:water (18:1:1, v/v/v) to give 0.11 g (70% yield) of the title compound as a white powder, m.p. 110°-112° C.; 1H NMR (d6 -DMSO) δ1.7 (q, 1H), 2.1-2.25 (m, 1H), 2.35-2.5 (m, 1H), 2.75-2.90 (m, 2H), 2.9-3.05 (m, 1H), 3.05-3.2 (m, 1H), 3.25-3.35 (m, 1H), 6.07 (d, 1H), 6.81 (d, 1H), 7.0 (t, 1H), 7.2-7.3 (m, 1H), 7.3-7.4 (m, 4H), 8.38 (s, 1H).

後処理

  1. temperatureto warm to ambient temperature
  2. temperaturethen cooled to -78° C
  3. temperatureto warm to ambient temperature
  4. concentrationthen concentrated in vacuo
  5. dissolutionThe residue was dissolved in methanol
  6. dissolutionThe residue was redissolved in methanol
  7. customthe methanol solution was chromatographed on a silica gel column
  8. washeluted with ethyl acetate:formic acid:water (18:1:1, v/v/v)

出典と根拠

ORDレコード
ord-77cc17c6ee2f4b9f9f2258d7588210bc
出典データセット
uspto-grants-1991_02
特許番号
US04994486

反応ノート

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