Boron tribromide → N-Acetyl-5-hydroxy-3,4,6-trimethylindoline

HRID 1488455ノート

反応式

HRID 1488455 の反応式
B(Br)(Br)Br.[C:5]([N:8]1[C:16]2[C:11](=[C:12]([CH3:20])[C:13]([O:18]C)=[C:14]([CH3:17])[CH:15]=2)[CH:10]([CH3:21])[CH2:9]1)(=[O:7])[CH3:6]>C(Cl)Cl>[C:5]([N:8]1[C:16]2[C:11](=[C:12]([CH3:20])[C:13]([OH:18])=[C:14]([CH3:17])[CH:15]=2)[CH:10]([CH3:21])[CH2:9]1)(=[O:7])[CH3:6]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 22905645N-Acetyl-5-methoxy-3,4,6-trimethylindoline

生成物 1

HCID 22905640N-Acetyl-5-hydroxy-3,4,6-trimethylindoline収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

Boron tribromide (1.4 mL of 1M solution in methylene chloride, 1.4 mmol) was added to a cooled (-78° C.) solution of indoline 9 (110 mg, 47 mmol) dissolved in methylene chloride (2 mL). The resulting solution was maintained at -78° C. (1 h), then slowly warmed to room temperature and held there for 17 h. The cooled reaction mixture was quenched with a few drops of methanol followed by cold water. The solution was extracted with methylene chloride and the combined organic layers were washed with brine and dried (MgSO4). Removal of solvents gave a solid, which was recrystallized from methylene chloride-hexanes to afford the indoline 11a (95 mg, 92% yield) as a colorless solid, mp 204°-205° C. Spectral data: 13C NMR (CD3SOCD3): δ 12.3, 17.2, 20.7, 23.7, 33.4, 56.4, 115.3, 120.7, 122.6, 133.9, 134.3, 149.1, 167.4; HRMS: calcd. for C13H17NO2 219.1259, fnd. 219.1261. Anal: calcd. for C13H17NO2C, 71.21, H, 7.81, N, 6.39, fnd. C, 71.06,H, 7.84, N, 6.33.

後処理

  1. temperatureslowly warmed to room temperature
  2. customThe cooled reaction mixture
  3. customwas quenched with a few drops of methanol
  4. extractionThe solution was extracted with methylene chloride
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. customRemoval of solvents
  8. customgave a solid, which
  9. customwas recrystallized from methylene chloride-hexanes

出典と根拠

ORDレコード
ord-7afa2fc7ce284a48af56f00b91df57bc
出典データセット
uspto-grants-1997_10
特許番号
US05674876

反応ノート

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