Ammonium Chloride → HCID 69307765, 화합물

HRID 2056742노트

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HRID 2056742 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 69307765HCID 69307765, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e075035d844c49a59bb5b73250aa9a50
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335660B2

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