Water → HCID 57263166, 화합물

HRID 2388669노트

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HRID 2388669 반응식
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][C@H:9]1[C:18](O)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.O1CCCC1.O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[OH:19][CH2:18][C@@H:9]1[CH2:10][CH2:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2723981Borane;tetrahydrofuranHCID 40425216(s)-1-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

생성물 1

HCID 57263166HCID 57263166, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(S)-1-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid (5 g, 18.03 mmol) was dissolved in tetrahydrofuran (40 ml) and the mixture was cooled. Boron hydride-tetrahydrofuran complex (27 ml, 1 mol/l in tetrahydrofuran) was cautiously added dropwise at 0° C. and the mixture was then stirred at room temperature for 15 h. The reaction mixture was cooled again and water (8 ml) was slowly added dropwise at 0° C. Potassium carbonate (4.21 g, 30.65 mmol) was then added and the mixture was stirred for 30 min. After phase separation the aqueous phase was extracted with diethyl ether (2×30 ml) and the combined organic phases were washed with saturated sodium chloride solution (30 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/ethyl acetate 2/1.

후처리

  1. temperaturethe mixture was cooled
  2. temperatureThe reaction mixture was cooled again
  3. stirringthe mixture was stirred for 30 min
  4. customAfter phase separation the aqueous phase
  5. extractionwas extracted with diethyl ether (2×30 ml)
  6. washthe combined organic phases were washed with saturated sodium chloride solution (30 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography (silica gel) with hexane/ethyl acetate 2/1

출처 및 근거

ORD 기록
ord-fb32430a42a44788a7c1fde72d6dc6e9
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268814B2

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