1-(tert-Butoxycarbonyl)piperidine-4-carboxamide → Tert-butyl 4-{4-[4-(methylsulfanyl)phenyl]-1,3-oxazol-2-yl}piperidine-1-carboxylate

HRID 716709ノート

反応式

HRID 716709 の反応式
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=O.[C:13]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)(=[O:15])[NH2:14]>CN1C(=O)N(C)CCC1>[CH3:12][S:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:14]=[C:13]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[O:15][CH:2]=2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 27356461-(tert-Butoxycarbonyl)piperidine-4-carboxamideHCID 27375232-Bromo-1-(4-methylsulfanylphenyl)ethanone

生成物 1

HCID 71207840Tert-butyl 4-{4-[4-(methylsulfanyl)phenyl]-1,3-oxazol-2-yl}piperidine-1-carboxylate収率 25.1%

試薬・触媒・溶媒 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

反応条件

温度
145 °C

実験手順

2-Bromo-1-[4-(methylsulfanyl)phenyl]ethanone (5 g, 19.15 mmol) and tert-butyl 4-carbamoylpiperidine-1-carboxylate (4.37 g, 19.15 mmol) were dissolved in DMPU (40.8 mL) and heated to 145° C. for 15 min. The resulting solution was then cooled to room temperature, partitioned between aqueous LiCl and ethyl acetate. The combined organics were dried over sodium sulfate and concentrated in vacuo. The resulting crude oil was purified using silica gel chromatography (300 g, using 20-80% ethyl acetate in hexane gradient) to yield 1.8 g of the desired product as a yellow oil. LCMS (M+1)=375.40

後処理

  1. temperatureThe resulting solution was then cooled to room temperature
  2. custompartitioned between aqueous LiCl and ethyl acetate
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude oil was purified

出典と根拠

ORDレコード
ord-5c00385fa3474bff98ae15ed7735f3ed
出典データセット
uspto-grants-2015_11
特許番号
US09193697B2

反応ノート

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