Formic Acid → Methyl 8-bromo-1-formyl-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate

HRID 402288ノート

反応式

HRID 402288 の反応式
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[Br:11][C:12]1[CH:13]=[CH:14][C:15]2[NH:22][CH2:21][CH2:20][CH2:19][C:18]([C:23]([O:25][CH3:26])=[O:24])=[CH:17][C:16]=2[CH:27]=1>C1COCC1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]2[N:22]([CH:1]=[O:2])[CH2:21][CH2:20][CH2:19][C:18]([C:23]([O:25][CH3:26])=[O:24])=[CH:17][C:16]=2[CH:27]=1

参加物

5

反応物 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 68650133Methyl 8-bromo-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate

生成物 1

HCID 86595586Methyl 8-bromo-1-formyl-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
55 °C

実験手順

Formic acid (5.96 ml) was added to acetic anhydride (12.2 ml) at 0° C. and then the mixture was stirred under nitrogen atmosphere at 55° C. for 2 hours. After cooling to 0° C., THF (150 ml) was added, and further a solution of methyl 8-bromo-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate (8.5 g) in THF (100 ml) was added dropwise under nitrogen atmosphere. The mixture was returned to room temperature and stirred for 5 hours, after which the solvent was distilled off under reduced pressure. The reaction material was diluted with ethyl acetate, followed by washing with saturated sodium bicarbonate, water and saturated brine. The resultant was dried with magnesium sulfate, after which the solvent was distilled off under reduced pressure, and the resulting residue was washed with hexane to give methyl 8-bromo-1-formyl-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate (8.3 g) as colorless crystals.

後処理

  1. temperatureAfter cooling to 0° C.
  2. customwas returned to room temperature
  3. stirringstirred for 5 hours
  4. distillationafter which the solvent was distilled off under reduced pressure
  5. additionThe reaction material was diluted with ethyl acetate
  6. washby washing with saturated sodium bicarbonate, water and saturated brine
  7. dry with materialThe resultant was dried with magnesium sulfate
  8. distillationafter which the solvent was distilled off under reduced pressure
  9. washthe resulting residue was washed with hexane

出典と根拠

ORDレコード
ord-a978320c98424ec1a0c208e39dd10efa
出典データセット
uspto-grants-2014_06
特許番号
US08741943B2

反応ノート

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