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

HRID 12820

反応式

HRID 12820 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
-30 °C

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-aab3b91cf6294126a849440ff6925f04
出典データセット
uspto-grants-2010_06
特許番号
US07728029B2

関連ノート

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