Triethylamine → t-Butyl 4-hydroxy-3-{[4-(trifluoromethyl)benzoyl]amino}piperidin-1-carboxylate

HRID 1360172ノート

反応式

HRID 1360172 の反応式
[NH2:1][CH:2]1[CH:7]([OH:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.C(N(CC)CC)C.[F:23][C:24]([F:34])([F:33])[C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1.C([O:37]C(=O)CC(C)=O)C>C(Cl)Cl>[OH:8][CH:7]1[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][CH:2]1[NH:1][C:29](=[O:37])[C:28]1[CH:31]=[CH:32][C:25]([C:24]([F:34])([F:33])[F:23])=[CH:26][CH:27]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 8868Ethyl AcetoacetateHCID 123096p-Trifluoromethylbenzyl chlorideHCID 56932104tert-Butyl 3-amino-4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 66969609t-Butyl 4-hydroxy-3-{[4-(trifluoromethyl)benzoyl]amino}piperidin-1-carboxylate収率 54%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

0.50 g (2.3 mmol) of t-butyl 3-amino-4-hydroxypiperidin-1-carboxylate (product of PREPARATION 83) and 0.32 mL, (2.3 mmol) of triethylamine was dissolved in 30 mL of methylene chloride, and 0.34 mL, (2.3 mmol) of 4-trifluoromethyl benzylchloride was dropwise added thereto while stirring at 0° C. for 1 hour, followed by addition of 100 mL of ethylacetoacetate and then washing with water. An organic layer dried over anhydrous magnesium sulfate. The reaction solution was filtered off and distilled off under reduced pressure, then the residue was purified by column chromatography to give 0.48 g (1.2 mmol) of the title compound in a total yield of 54%.

後処理

  1. washwashing with water
  2. dry with materialAn organic layer dried over anhydrous magnesium sulfate
  3. filtrationThe reaction solution was filtered off
  4. distillationdistilled off under reduced pressure
  5. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-a454667cf7a94e6a9fac05800c786047
出典データセット
uspto-grants-2011_02
特許番号
US07879848B2

反応ノート

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