Hydrogen Bromide → (-)-(cis)-7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine

HRID 1668357ノート

反応式

HRID 1668357 の反応式
Br.[Br:2][C:3]1[C:27]([F:28])=[CH:26][C:6]2[O:7][C:8]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:9]=3[C@H:10]3[C@H:15]([NH:16]C(=O)OC)[CH2:14][CH2:13][CH2:12][N:11]3[C:5]=2[CH:4]=1.[OH-].[Na+]>C(O)(=O)C>[Br:2][C:3]1[C:27]([F:28])=[CH:26][C:6]2[O:7][C:8]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:9]=3[C@H:10]3[C@H:15]([NH2:16])[CH2:14][CH2:13][CH2:12][N:11]3[C:5]=2[CH:4]=1

参加物

5

反応物 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 86619614methyl (+/-)-(cis)-(7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate

生成物 1

HCID 67359100(-)-(cis)-7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine収率 87.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

A mixture of acetic acid (80 mL) and hydrogen bromide (48%, 40 mL) was added to methyl (±)-(cis)-(7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate (38.2 mmol), and the mixture stirred overnight at 100° C. After cooling down the reaction mixture was poured into a cold 1N NaOH solution (pH 9). It was extracted with ethyl acetate and the organic layer was washed with brine, dried (Na2SO4) and the solvent was evaporated under reduced pressure to yield the crude title compound (12.7 g, 87%) which was used without further purification. (m/z)=381+383 (M+H)+.

後処理

  1. temperatureAfter cooling down the reaction mixture
  2. extractionIt was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-19cefacc63994b60876e97209bb19297
出典データセット
uspto-grants-2011_08
特許番号
US07989442B2

反応ノート

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