Water → trans-(4-Azido-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

HRID 39419

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HRID 39419 반응식
[C:1]([O:5][C:6]([N:8]1[CH:14]2[CH:9]1[CH2:10][CH2:11][O:12][CH2:13]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl([O-])(=O)(=O)=O.[Li+].[N-:21]=[N+:22]=[N-:23].[Na+].O>C(#N)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:14]1[C@H:9]([N:21]=[N+:22]=[N-:23])[CH2:10][CH2:11][O:12][CH2:13]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 33557Sodium AzideHCID 23665649Lithium perchlorateHCID 58381262Tert-butyl 3-oxa-7-azabicyclo[4.1.0]heptane-7-carboxylate2회

생성물 1

HCID 86656338trans-(4-Azido-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester수율 52.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

3-Oxa-7-aza-bicyclo[4.1.0]heptane-7-carboxylic acid tert-butyl ester (intermediate E) (5.2 g, 26 mmol) was dissolved in 100 mL acetonitrile. Lithium perchlorate (23 g, 207 mmol) and sodium azide (6.8 g, 104 mmol) were added and the reaction mixture was stirred at 80° C. overnight. 200 mL Water was added. The mixture was extracted three times with diethylether. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (heptane/ethyl acetate 1:0→1:1) yielded the title compound as a colorless oil (3.3 g, 52%), MS: m/e=186 [(M-butene)+].

후처리

  1. extractionThe mixture was extracted three times with diethylether
  2. customThe combined organic phases were dried on sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customPurification of the residue by flash chromatography on silica gel (heptane/ethyl acetate 1:0→1:1)

출처 및 근거

ORD 기록
ord-5c9dd2f5be3748d3b48fc749a9973630
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524909B2

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