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Ammonium Hydroxide → Benzyl 2-(4-chlorophenyl)-4-oxopiperidine-1-carboxylate

HRID 15729
ノート
印刷プレビュー

反応式

HRID 15729 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[B-](F)(F)(F)[O+](C)C.[O:17]=[C:18]1[CH:23]=[CH:22][N:21]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:20][CH2:19]1.[NH4+].[Cl-].[NH4+].[OH-]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:22]2[CH2:23][C:18](=[O:17])[CH2:19][CH2:20][N:21]2[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])=[CH:4][CH:3]=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

8

反応物 5

HCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 11368235Benzyl 3,4-dihydro-4-oxo-pyridine-1(2H)-carboxylateHCID 178478191HCID 178478191、化合物HCID 178494437HCID 178494437、化合物

生成物 1

HCID 59342393Benzyl 2-(4-chlorophenyl)-4-oxopiperidine-1-carboxylate

試薬・触媒・溶媒

2
HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

CuBr.SMe2 complex (1.49 g, 7.26 mmol) was added to 25 mL of anhydrous THF and cooled to −78° C. 4-Chlorophenylmagnesium bromide (7.26 mL, 1.0 M in THF, 7.26 mmol) was added slowly via syringe. Stirring at −78° C. for 1 hour produced an orange then green-like suspension. Boron trifluoride dimethyl etherate (0.92 mL, 7.26 mmol) was added and stirred for 5 minutes. To the newly formed complex was then added over 1 hour a solution of the compound 66 (1.0 g, 4.32 mmol) in 15 mL of anhydrous THF. After stirring 2 hours at −78° C., 16 mL of aq. 20% NH4Cl/conc. NH4OH (1:1) was added, and the mixture was allowed to warm-up to room temperature. EtOAc was used to extract (3×100 mL) and the combined organic layers were washed with brine and dried (MgSO4). Solvent was removed by rotary evaporation and the residue was purified by flash chromatography to give the product 67 as a colorless oil.

後処理

  1. customproduced an orange then green-like suspension
  2. stirringstirred for 5 minutes
  3. stirringAfter stirring 2 hours at −78° C.
  4. temperatureto warm-up to room temperature
  5. extractionto extract (3×100 mL)
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. customSolvent was removed by rotary evaporation
  9. customthe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-ab71bfae619241b3a6352d150f024773
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07732609B2

反応ノート

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