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

HRID 1668348노트

반응식

HRID 1668348 반응식
Br.[Br:2][C:3]1[C:26]([F:27])=[CH:25][C:6]2[O:7][C:8]3[CH:24]=[CH:23][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:26]([F:27])=[CH:25][C:6]2[O:7][C:8]3[CH:24]=[CH:23][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

참가 물질

5

반응물 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 86619612Methyl (+/-)-(cis)-(7-bromo-8-fluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate

생성물 1

HCID 67358773(-)-(cis)-7-bromo-8-fluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-amine수율 91.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

A mixture of acetic acid (40 mL) and hydrogen bromide (48%, 20 mL) was added to methyl (±)-(cis)-(7-bromo-8-fluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate (20.2 g, 48 mmol) and stirred overnight at 100° C. After cooling down the reaction mixture was poured into a cold 1M NaOH solution. It was extracted with CH2Cl2 and the organic layer was washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure to yield the crude title compound (15.9 g, 91%) which was used without further purification. (m/z)=363+365 (M+H)+.

후처리

  1. temperatureAfter cooling down the reaction mixture
  2. extractionIt was extracted with CH2Cl2
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-83d555a260a44215886c29c9c1eac2dd
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989442B2

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