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Lawesson's reagent → tert-Butyl[(3S,5S,6R)-6-methyl-5-phenyl-2-thioxopiperidin-3-yl]carbamate

HRID 2179465
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HRID 2179465 반응식
[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:11]([CH3:20])[NH:10][C:9]1=O)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:11]([CH3:20])[NH:10][C:9]1=[S:32])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

4

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HCID 87949Lawesson's reagentHCID 69096668tert-butyl N-((3S,5S,6R)-6-methyl-2-oxo-5-phenylpiperidin-3-yl)carbamate

생성물 1

HCID 131732078tert-Butyl[(3S,5S,6R)-6-methyl-5-phenyl-2-thioxopiperidin-3-yl]carbamate수율 170.1%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
40 °C

실험 절차

To a solution of tert-butyl[(3S,5S,6R)-6-methyl-2-oxo-5-phenylpiperidin-3-yl]carbamate (796 mg, 2.62 mmol) in toluene (26.2 mL) was added Lawesson's Reagent (539 mg, 1.33 mmol) and the resulting mixture stirred at 40° C. 16 h. The mixture was cooled to ambient temperature and concentrated. Purification by silica gel chromatography (100% hexanes→60% hexanes/ethyl acetate) gave the title compound (725 mg). MS 343.3 (M+Na).

후처리

  1. custom16 h
  2. temperatureThe mixture was cooled to ambient temperature
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (100% hexanes→60% hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-4615c23399f4456e8aa2119f0ad47bf3
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09067941B2

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