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

HRID 1620603ノート

反応式

HRID 1620603 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-985be7839fce482db320661b9f863cce
出典データセット
uspto-grants-2014_07
特許番号
US08772277B2

反応ノート

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