Triethylamine → 1-[2,4-Bis(trifluoromethyl)benzyl]-4-(hydroxymethyl)piperidin-2-one

HRID 1620603노트

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HRID 1620603 반응식
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12](O)=[O:13])[CH2:8][C:7]1=[O:15].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.O>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][OH:13])[CH2:8][C:7]1=[O:15]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 866787731-[2,4-Bis(trifluoromethyl)benzyl]-2-oxopiperidine-4-carboxylic acid

생성물 1

HCID 866787741-[2,4-Bis(trifluoromethyl)benzyl]-4-(hydroxymethyl)piperidin-2-one수율 67.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]-2-oxopiperidine-4-carboxylic acid (16.8 g) and triethylamine (9.8 mL) in tetrahydrofuran (200 mL) was added ethyl chloroformate (8.0 mL) under cooling to 0° C. under a nitrogen atmosphere. The reaction mixture was stirred for 1 hr under cooling to 0° C., sodium borohydride (5.18 g) was added, and the mixture was further stirred at 30° C. overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (10.9 g).

후처리

  1. temperatureunder cooling to 0° C.
  2. stirringthe mixture was further stirred at 30° C. overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

출처 및 근거

ORD 기록
ord-985be7839fce482db320661b9f863cce
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772277B2

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