Hydrochloric Acid → HCID 86729751, 화합물

HRID 2272592

반응식

HRID 2272592 반응식
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH2:16])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].C[Al](C)C.[OH:21][C:22]1([CH3:29])[CH2:27][CH2:26][O:25][C:24](=[O:28])[CH2:23]1.Cl>C1(C)C=CC=CC=1>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][C:24](=[O:28])[CH2:23][C:22]([OH:21])([CH3:29])[CH2:27][CH2:26][OH:25])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 85883-Amino-9-ethylcarbazoleHCID 10428(+-)-MevalonolactoneHCID 16682925Trimethylaluminum

생성물 1

HCID 86729751HCID 86729751, 화합물수율 74%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

To a solution of 9-ethyl-9H-carbazol-3-amine (300 mg, 1.43 mmol) in toluene (4 mL) was added trimethylaluminium (1.8M in toluene solution, 1.189 mL, 2.14 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added a solution of 4-hydroxy-4-methyltetrahydro-2H-pyran-2-one (186 mg, 1.43 mmol) in toluene (4 mL) at room temperature, and the mixture was stirred at 80° C. for 4 hr. The reaction mixture was cooled to 0° C., neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane) to give N-(9-ethyl-9H-carbazol-3-yl)-3,5-dihydroxy-3-methylpentanamide (359 mg, 1.056 mmol, 74.0%) as a colorless oil.

후처리

  1. stirringthe mixture was stirred at 80° C. for 4 hr
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-c4387e4ab56f497e9361dcd751b5d166
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120776B2

연결된 노트

불러오는 중…