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Borane → HCID 57655963, 화합물

HRID 2041342
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HRID 2041342 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28](O)=[O:29])=[CH:24][CH:23]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([CH2:28][OH:29])=[CH:26][CH:27]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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HCID 6331BoraneHCID 576565513-tert-butoxycarbonyl-6-(4-carboxybenzylthio)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

생성물 1

HCID 57655963HCID 57655963, 화합물수율 54.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 3-tert-butoxycarbonyl-6-(4-carboxybenzylthio)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.85 g, 50% purity, 2.06 mmol) in anhydrous THF (40 mL) under nitrogen, add with stirring 1M borane in THF (4.2 mL) at 0° C. Warm to ambient temperature and stir 2-3 h. Quench by the careful addition of water (3 mL), dilute with saturated aqueous NaHCO3, extract three times with ethyl ether, dry over anhydrous MgSO4, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (5:1) to provide the title compound as a white solid (485 mg, 54%).

후처리

  1. customQuench by the careful addition of water (3 mL)
  2. additiondilute with saturated aqueous NaHCO3
  3. extractionextract three times with ethyl ether
  4. dry with materialdry over anhydrous MgSO4
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel eluting with hexane/EtOAc (5:1)

출처 및 근거

ORD 기록
ord-10743b8fda774aa39025c1df4db984d1
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08580780B2

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