Pyridine → N-nitroso-N-(tert-butoxycarbonyl)amino-cyclopropane

HRID 12820

반응식

HRID 12820 반응식
F[B-](F)(F)F.[N:6]#[O+:7].[C:8]([O:12][C:13]([NH:15][CH:16]1[CH2:18][CH2:17]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].N1C=CC=CC=1.CCOC(C)=O>C(#N)C>[N:6]([N:15]([CH:16]1[CH2:18][CH2:17]1)[C:13]([O:12][C:8]([CH3:11])([CH3:9])[CH3:10])=[O:14])=[O:7]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 11137142Nitrilooxonium tetrafluoroborateHCID 15698228tert-Butyl N-cyclopropylcarbamate

생성물 1

HCID 57941319N-nitroso-N-(tert-butoxycarbonyl)amino-cyclopropane수율 106.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
-30 °C

실험 절차

Nitrosonium tetrafluoroborate (9.32 g, 79.8 mmol) was added carefully in several portions to a cooled (−30° C.) solution of N-(tert-butoxycarbonyl)cyclopropylamine (9.57 g, 60.9 mmol) and anhydrous pyridine (11.7 mL) in dry acetonitrile (150 mL). The solution was stirred at −30° C. for 30 minutes, and then at 0° C. for 2 hours. Ice water and EtOAc were added and the organic phase was separated and washed quickly with 1N HCl to remove pyridine. The organic phase was washed with 1N NaHCO3 and brine, dried (MgSO4), filtered, and evaporated under high vacuum with a water bath temperature below 40° C. to give N-nitroso-N-(tert-butoxycarbonyl)amino-cyclopropane (12.1 g, quantitative) as an oil.

후처리

  1. waitat 0° C. for 2 hours
  2. customthe organic phase was separated
  3. washwashed quickly with 1N HCl
  4. customto remove pyridine
  5. washThe organic phase was washed with 1N NaHCO3 and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated under high vacuum with a water bath temperature below 40° C.

출처 및 근거

ORD 기록
ord-aab3b91cf6294126a849440ff6925f04
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728029B2

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