Potassium Carbonate → tert-Butyl{1-[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]piperidin-4-yl}carbamate

HRID 1644407ノート

反応式

HRID 1644407 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:22]/[CH:23]=[CH:24]/[C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[F:32]>C(O)C>[C:10]([O:9][C:8](=[O:14])[NH:7][CH:4]1[CH2:3][CH2:2][N:1]([CH2:22]/[CH:23]=[CH:24]/[C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])[CH2:6][CH2:5]1)([CH3:11])([CH3:13])[CH3:12]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 11608064(E)-2-(3-Chloroprop-1-en-1-yl)-1,4-difluorobenzene2 回

生成物 1

HCID 86642637tert-Butyl{1-[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]piperidin-4-yl}carbamate収率 70.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

A mixture of tert-butyl piperidin-4-ylcarbamate (248 mg, 1.2 mmol), potassium carbonate (188 mg, 1.4 mmol) and 2-[(1E)-3-chloroprop-1-en-1-yl]-1,4-difluorobenzene (Intermediate 124, 257 mg, 1.4 mmol) in ethanol (7 mL) was heated to 80° C. for 18 hours. The mixture was concentrated under reduced pressure, the residue taken up in dichloromethane (20 mL) and water (20 mL), the aqueous phase was back extracted with dichloromethane (2×20 mL) and the combined organic phases were dried over sodium sulfate. Chromatography on silica gel with dichloromethane/methanol (95:5) gave 300 mg (69%) of product as a brown foam.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionwater (20 mL), the aqueous phase was back extracted with dichloromethane (2×20 mL)
  3. dry with materialthe combined organic phases were dried over sodium sulfate

出典と根拠

ORDレコード
ord-3429e9fe41e04ecb860dd11907b92135
出典データセット
uspto-grants-2012_02
特許番号
US08124602B2

反応ノート

読み込み中…