1,4-Dibromobutane → trans-(4-Pyrrolidin-1-yl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

HRID 39421

반응식

HRID 39421 반응식
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[C@H:13]([NH2:14])[CH2:12][CH2:11][O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26]Br>C(#N)C>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[C@H:13]([N:14]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:12][CH2:11][O:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 67358958HCID 67358958, 화합물2회

생성물 1

HCID 67358972trans-(4-Pyrrolidin-1-yl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester수율 84%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

trans-(4-Amino-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (intermediate G, 330 mg, 1.53 mmol) was dissolved in 8 mL acetonitrile. Potassium carbonate (1.05 g, 7.6 mmol) and 1,4-dibromobutane (672 mg, 3.11 mmol) were added and the reaction mixture was refluxed overnight. The solvent was evaporated off. The residue was taken up in water and 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 (dichloromethane/methanol/ammonia 1:0:0→140:10:1) yielded the title compound as a yellow oil (347 mg, 84%), MS: m/e=271.3 [(M+H)+].

후처리

  1. temperaturethe reaction mixture was refluxed overnight
  2. customThe solvent was evaporated off
  3. extractionextracted three times with diethylether
  4. customThe combined organic phases were dried on sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 1:0:0→140:10:1)

출처 및 근거

ORD 기록
ord-3fea5b1e26de4ca2a508db93057c2192
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524909B2

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