Hydrochloric Acid → 3-(4-Tert-butoxycarbonylaminophenyl)propanol

HRID 1978392노트

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HRID 1978392 반응식
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([O:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](OCC)=[O:28])=[CH:21][CH:20]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].Cl>O1CCCC1>[C:11]([O:15][C:16]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH2:27][OH:28])=[CH:23][CH:24]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 21994026Ethyl 3-(4-tert-butoxycarbonylaminophenyl)propionate

생성물 1

HCID 219940133-(4-Tert-butoxycarbonylaminophenyl)propanol수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Diisobutylaluminium hydride(l.5 M in toluene, 30.5 ml, 45.8 mmol) was added dropwise to a stirred solution of ethyl 3-(4-tert-butoxycarbonylaminophenyl)propionate (6.10 g, 20.8 mmol) in tetrahydrofuran (60 ml) at 0° C. and the mixture was stirred at 0° C. for 1 hour. 2N-hydrochloric acid was added to the mixture and the mixture was extracted with ethyl acetate. The extract was successively washed with water, saturated aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (3:2) to give 3-(4-tert-butoxycarbonylaminophenyl)propanol as a colorless oil (2.66 g, 51%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was successively washed with water, saturated aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (3:2)

출처 및 근거

ORD 기록
ord-2707dce753ee478ba7fbac6412c6619f
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235731B1

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