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Ethanol → 5-(5-Fluoro-2-methoxyphenyl)-5-methyl-2-(2-methylquinolin-5-ylamino)-3-(trifluoromethyl)hexan-3-ol

HRID 2055029
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HRID 2055029 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH3:33])=[C:6]([C:8]([CH3:31])([CH3:30])[CH2:9][C:10]([C:26]([F:29])([F:28])[F:27])([OH:25])[C:11](=[N:13][C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([CH3:24])=[N:19]3)[CH3:12])[CH:7]=1.C(O)C.[BH4-].[Na+].[Na+].[Cl-]>O1CCCC1.[Ti]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH3:33])=[C:6]([C:8]([CH3:30])([CH3:31])[CH2:9][C:10]([C:26]([F:27])([F:28])[F:29])([OH:25])[CH:11]([NH:13][C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([CH3:24])=[N:19]3)[CH3:12])[CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 702EthanolHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 219489245-(5-Fluoro-2-methoxyphenyl)-5-methyl-2-(2-methylquinolin-5-ylimino)-3-(trifluoromethyl)hexan-3-ol

생성물 1

HCID 219488865-(5-Fluoro-2-methoxyphenyl)-5-methyl-2-(2-methylquinolin-5-ylamino)-3-(trifluoromethyl)hexan-3-ol수율 29.3%

시약·촉매·용매 2

HCID 23963Titanium촉매HCID 8028Tetrahydrofuran용매

실험 절차

231 mg (0.5 mmol) of 5-(5-fluoro-2-methoxyphenyl)-5-methyl-2-(2-methylquinolin-5-ylimino)-3-(trifluoromethyl)hexan-3-ol is mixed in 10 ml of tetrahydrofuran and 4 ml of ethanol with 0.21 ml (1 mmol) of titanium tetraethylate. Then, 875 mg (23.1 mmol) of sodium borohydride is added in portions within 4 days at a reaction temperature of 65° C. The reaction mixture is mixed with 20 ml of saturated NaCl solution after cooling to room temperature, stirred for 1 hour at room temperature, filtered on Celite, and rewashed with ethyl acetate and tetrahydrofuran. The organic phase is separated, washed with saturated NaCl solution, dried and concentrated by evaporation. Column chromatography on silica gel with hexane-ethyl acetate yields 68 mg of the product as a mixture of the two possible diastereomers.

후처리

  1. filtrationfiltered on Celite
  2. customThe organic phase is separated
  3. washwashed with saturated NaCl solution
  4. customdried
  5. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-e23ad2247fda44beae76343bc2fd00f2
출처 데이터셋
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07329753B2

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