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Potassium Cyanide → HCID 22458268, 화합물

HRID 2185568
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HRID 2185568 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:24])[CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[Li+].[I-].[C-:27]#[N:28].[K+].C([O-])([O-])=O.[K+].[K+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>CS(C)=O.CCOC(C)=O>[C:27]([C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:24])[CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1)#[N:28]
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참가 물질

8

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HCID 9032Potassium CyanideHCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 90495Di-tert-butyl dicarbonateHCID 22458227HCID 22458227, 화합물

생성물 1

HCID 22458268HCID 22458268, 화합물수율 12%

시약·촉매·용매 2

HCID 679
Dimethyl Sulfoxide
용매
HCID 8857Ethyl Acetate용매

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온도
135 °C

실험 절차

A round bottom flask was charged with 4-(3-(4-fluoro-phenyl)-3-oxopropyl)-1-tert-butoxycarbonyl-piperidine (614 mg, 1.83 mmol, from Step C), LiI, (294 mg, 2.2 mmol), KCN (358 mg, 5.5 mmol), and K2CO3 (3 grams, 22 mmol) in 30 mL DMSO. The mixture was heated to 135° C. for 72 h. The solution was cooled to room temperature and di-tert-butyl dicarbonate (500 mg, 2.3 mmol) was added. After 1 h the mixture was diluted with 100 mL EtOAc and the organic phase washed with water (50 mL) and sat'd NaCl (2×50 mL), then dried over Na2SO4 and concentrated. Flash chromatography (3/1 hexane/EtOAc eluant) afforded 75 mg (12%) of the title compound.

후처리

  1. temperatureThe solution was cooled to room temperature
  2. washthe organic phase washed with water (50 mL) and sat'd NaCl (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8c74b62cf5d9418b96edc19b4c0bdd51
출처 데이터셋
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06399619B1

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