Triethylamine → HCID 68328080, 화합물

HRID 2281244노트

반응식

HRID 2281244 반응식
Cl[C:2](Cl)([O:4][C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[Br:13][C:14]1[CH:15]=[C:16]([CH2:20][NH2:21])[CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C.[N:29]12[CH2:36]C[CH:32]([CH2:33][CH2:34]1)[CH:31](O)[CH2:30]2>C1COCC1>[Br:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[CH2:20][NH:21][C:5](=[O:11])[O:4][CH:2]1[CH:32]2[CH2:33][CH2:34][N:29]([CH2:30][CH2:31]2)[CH2:36]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 15381(+-)-3-QuinuclidinolHCID 94429TriphosgeneHCID 457587Benzenemethanamine, 3-bromo-

생성물 1

HCID 68328080HCID 68328080, 화합물수율 74.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred and cooled (0° C.) solution of triphosgene (0.80 g, 2.7 mmol) in THF (20 mL) was added, dropwise, a mixture of (3-bromophenyl)methanamine (1.0 g, 5.4 mmol) and triethylamine (1.08 g, 10.7 mmol) in THF (30 mL) over 2 h. After the addition was complete, the mixture was refluxed for 1 h and then cooled to room temperature. Quinuclidin-3-ol (1.40 g, 10.7 mmol) was added, and the mixture was refluxed for 18 h. The solvent was removed in vacuo, and the residue was dissolved in EtOAc, washed with water, dried over Na2SO4, and concentrated. The crude residue was purified by silica gel column chromatography (eluting with EtOAc/methanol=10/1) to give quinuclidin-3-yl 3-bromobenzylcarbamate as a colourless liquid (0.68 g, 37%).

후처리

  1. additionwas added
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 1 h
  4. temperaturethe mixture was refluxed for 18 h
  5. customThe solvent was removed in vacuo
  6. dissolutionthe residue was dissolved in EtOAc
  7. washwashed with water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe crude residue was purified by silica gel column chromatography (eluting with EtOAc/methanol=10/1)

출처 및 근거

ORD 기록
ord-483e2340512c4234933785d2aaf7787e
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139580B2

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