Triethylamine → 4-Piperidinemethanol, 1-benzoyl-

HRID 278248

反応式

HRID 278248 の反応式
[C:1]([N:9]1[CH2:17][CH2:16][CH:12]([C:13](O)=[O:14])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.CN(C=O)C.O>[OH:14][CH2:13][CH:12]1[CH2:11][CH2:10][N:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16]1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 789351-Benzoylpiperidine-4-carboxylic acidHCID 4311764Sodium borohydride

生成物 1

HCID 102628704-Piperidinemethanol, 1-benzoyl-収率 99.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 2 g of 1-benzoylisonipecotic acid (Step A) in 50 mL THF at 0° C. were added 1.47 g of triethylamine and 1.99 g of isobutyl chloroformate. The reaction was stirred for 1 h at 0° C. To a solution of 1.10 g of sodium borohydride in 30 mL DMF at 0° C. was slowly added the above THF mixture. The reaction was again stirred for 1 h at 0° C. Water (80 mL) was slowly added to the reaction and the mixture was extracted 5×80 mL ethyl acetate and the combined organic layers were dried over magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by flash chromatography with 1:1 hexane : ethyl acetate followed by hexane : ethyl acetate: methanol, 50:50:5 to give 1.865 g of the title compound.

後処理

  1. stirringThe reaction was again stirred for 1 h at 0° C
  2. extractionthe mixture was extracted 5×80 mL ethyl acetate
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe residue was purified by flash chromatography with 1:1 hexane

出典と根拠

ORDレコード
ord-ac9768a399e142d29cfd64358aaa3407
出典データセット
uspto-grants-2002_03
特許番号
US06358979B1

関連ノート

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