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Ethyl Acetate → tert-Butyl 4-(5-(trifluoromethyl)pyridin-2-ylamino)piperidine-1-carboxylate

HRID 75105
ノート
印刷プレビュー

反応式

HRID 75105 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O.O>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([NH:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)=[N:3][CH:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 27364342-Bromo-5-(trifluoromethyl)pyridine

生成物 1

HCID 58576452tert-Butyl 4-(5-(trifluoromethyl)pyridin-2-ylamino)piperidine-1-carboxylate収率 83.3%

試薬・触媒・溶媒 2

HCID 679
Dimethyl Sulfoxide
溶媒
HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 0.678 g (3 mmol) of 2-bromo-5-(trifluoromethyl)pyridine, 0.901 g (4.5 mmol) of tert-butyl 4-aminopiperidine-1-carboxylate and 0.829 g (6 mmol) of potassium carbonate in 5 ml of dimethyl sulphoxide is heated at 100° C. for 20 hours. The mixture is cooled to ambient temperature and then 50 ml of ethyl acetate and 15 ml of water are added. The organic phase is separated by settling and washed twice with 15 ml of water and then with 15 ml of a saturated aqueous sodium chloride solution. It is dried over sodium sulphate and evaporated under vacuum. The product is purified by chromatography on silica gel, elution being carried out with a 20:80 and then 30:70 mixture of ethyl acetate and cyclohexane in order to obtain 0.864 g (2.5 mmol) of product in the form of a white solid.

後処理

  1. temperatureThe mixture is cooled to ambient temperature
  2. customThe organic phase is separated
  3. washwashed twice with 15 ml of water
  4. dry with materialIt is dried over sodium sulphate
  5. customevaporated under vacuum
  6. customThe product is purified by chromatography on silica gel, elution
  7. addition30:70 mixture of ethyl acetate and cyclohexane in order

出典と根拠

ORDレコード
ord-9d9fb918e31e49c8ae43b43b85cd4bb9
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08835418B2

反応ノート

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