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Ammonium Chloride → tert-butyl (8aS)-7-(3-fluorobenzyl)-6-oxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

HRID 240458
ノート
印刷プレビュー

反応式

HRID 240458 の反応式
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][CH:5]2[CH2:4][CH2:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=1.[NH4+].[Cl-]>O1CCCC1>[F:36][C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][CH:33]=1)[CH2:29][CH:3]1[C:2](=[O:1])[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C@@H:5]2[CH2:4]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 680073-Fluorobenzyl bromideHCID 2733832Lithium hexamethyldisilazaneHCID 82863310tert-butyl 6-oxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

生成物 1

HCID 86680467tert-butyl (8aS)-7-(3-fluorobenzyl)-6-oxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate収率 52%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-40 °C

実験手順

To a solution of the product from Example 207A (0.10 g, 0.416 mmol) in anhydrous tetrahydrofuran (4 mL) at −78° C. under N2 was added a 1 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (0.458 mL, 0.458 mmol) dropwise over 2 minutes. To the resulting solution was added 1-(bromomethyl)-3-fluorobenzene (0.056 mL, 0.458 mmol), and the resulting mixture was stirred at −40° C. for 3 hours. A solution of NH4Cl (10% in water, 1 mL) was added, and the mixture was allowed to warm to room temperature and partitioned between water and ethyl acetate (3×). The combined organic layers were dried over Na2SO4. The drying agent was removed by filtration, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-10% CH3OH in CH2Cl2 to give the title compound (75 mg, 52%).

後処理

  1. temperatureto warm to room temperature
  2. custompartitioned between water and ethyl acetate (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-10% CH3OH in CH2Cl2

出典と根拠

ORDレコード
ord-8cddb0b7e6d341ca8405a75ed815e58c
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08648074B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート