Ammonium Chloride → HCID 69307765、化合物

HRID 2056742ノート

反応式

HRID 2056742 の反応式
Br[C:2]1[C:12]2[C:13]3[C:5]([CH:6]=[CH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.C([Li])CCC.[O:19]=[C:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1.[Cl-].[NH4+]>C1COCC1>[CH2:7]1[C:8]2=[C:13]3[C:12](=[CH:11][CH:10]=[CH:9]2)[C:2]([C:20]2([OH:19])[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:24][CH2:25]2)=[CH:3][CH:4]=[C:5]3[CH2:6]1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 122444035-BromoacenaphthyleneHCID 178418339Butyllithium

生成物 1

HCID 69307765HCID 69307765、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 5-bromoacenaphthylene (1.00 g, 4.29 mmol) in dry THF (20 mL), under nitrogen at −78° C., was added a solution of n-butyllithium (2.5M in hexanes) (1.89 mL, 4.72 mmol) over a period of 30 min. The resulting deep red solution was left to stir for a further 30 minutes at −78° C. A solution of tert-butyl 4-oxo-1-piperidinecarboxylate (0.94 g, 4.72 mmol) in dry THF (10 mL) was then added over 30 min. After 2.5 h a cooled solution of saturated ammonium chloride (30 mL) was added, the reaction mixture allowed to warm to room temperature and then extracted with diethyl ether. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to yield a thick, yellowish tan oil. This oil was purified by flash chromatography on silica, eluting with a methanol/dichloromethane gradient, to yield tert-butyl 4-(1,2-dihydro-5-acenaphthylenyl)-4-hydroxy-1-piperidinecarboxylate as a sticky yellow residue.

後処理

  1. waitThe resulting deep red solution was left
  2. temperatureto warm to room temperature
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto yield a thick, yellowish tan oil
  7. customThis oil was purified by flash chromatography on silica
  8. washeluting with a methanol/dichloromethane gradient

出典と根拠

ORDレコード
ord-e075035d844c49a59bb5b73250aa9a50
出典データセット
uspto-grants-2008_02
特許番号
US07335660B2

反応ノート

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