Ammonium Chloride → 1-Tert-butoxycarbonyl-4-[2-(4-methylphenylsulfanyl)phenyl]piperidin-4-ol

HRID 1527999노트

반응식

HRID 1527999 반응식
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].[NH4+].[Cl-]>C1COCC1>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C:31]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)([OH:34])[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 21864904(2-Bromophenyl)(p-tolyl)sulfaneHCID 178418339Butyllithium

생성물 1

HCID 218649151-Tert-butoxycarbonyl-4-[2-(4-methylphenylsulfanyl)phenyl]piperidin-4-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of BuLi (2.5 M in hexane, 12.0 ml, 30 mmol) was slowly added to a stirred solution of 1-bromo-2-(4-methylphenylsulfanyl)benzene (30 mmol) in dry THF (75 ml) under Argon at −78° C. The solution was stirred for 10 min before 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (5.98 g, 30 mmol) was added in one portion. The solution was allowed to warm up to room temperature and then stirred for 3 h. Saturated aqueous NH4Cl (150 ml) was added and the solution was extracted with ethylacetate (150 ml). The organic phase was washed with brine, dried (MgSO4) and the solvent was evaporated in vacuo. Crude 1 was purified by flash chromatography on silica gel (eluent: Ethylacetat/heptane 20:80) to produce the target compound as a white foam. LC/MS (m/z) 399.3 (MH+); RT=3.82; purity (UV, ELSD): 98%, 100%; yield: 5.02 g (42%).

후처리

  1. additionwas added in one portion
  2. extractionthe solution was extracted with ethylacetate (150 ml)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated in vacuo
  6. customCrude 1 was purified by flash chromatography on silica gel (eluent: Ethylacetat/heptane 20:80)

출처 및 근거

ORD 기록
ord-f799291219fa47d49137c298c748a4d9
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090575B2

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