Sodium hydride → HCID 178453877, 화합물

HRID 500091

반응식

HRID 500091 반응식
[H-].[Na+].[Br-].[CH:4]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:6][CH2:5]1.[CH:26]([C@H:28]1[CH2:33][CH2:32][C@H:31]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:30][CH2:29]1)=O.COCCOCCN(CCOCCOC)CCOCCOC.[Cl-].[NH4+]>O1CCCC1>[C:4]1(=[CH:26][C@H:28]2[CH2:33][CH2:32][C@H:31]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:30][CH2:29]2)[CH2:6][CH2:5]1

참가 물질

7

반응물 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 2723931Cyclopropyltriphenylphosphonium bromideHCID 178453955HCID 178453955, 화합물

생성물 1

HCID 178453877HCID 178453877, 화합물수율 43.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a mixture of sodium hydride (1.06 g) and anhydrous tetrahydrofuran (50 ml) was added cyclopropyl-triphenylphosphonium bromide (10.13 g), the mixture was heated under reflux for 1 hour. The reaction mixture was cooled to ambient temperature, and then thereto was added a mixture of t-butyl trans-4-formylcyclohexylcarbamate (3.00 g), tris[2-(2-methoxyethoxy)ethyl]amine (427 mg) and anhydrous tetrahydrofuran (15 ml). The resulting mixture was heated under reflux for 1 hour. The reaction mixture was cooled to ambient temperature, and then saturated aqueous ammonium chloride was added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) to give 1.43 g of t-butyl trans-4-cyclopropylidenemethylcyclohexylcarbamate.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. additionwas added
  4. temperatureThe resulting mixture was heated
  5. temperatureunder reflux for 1 hour
  6. temperatureThe reaction mixture was cooled to ambient temperature
  7. extractionThe reaction mixture was extracted with ethyl acetate
  8. washthe organic layer was washed with brine
  9. dry with materialdried over sodium sulfate
  10. customthe solvent was removed in vacuo
  11. customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)

출처 및 근거

ORD 기록
ord-9270142efa654b0cbefa7320fe97f2c8
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767854B2

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