N-methyl-2-pyrrolidone → HCID 68579778、化合物

HRID 2233900ノート

反応式

HRID 2233900 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].O1C=[CH:29][CH:28]=[C:27]1P(C1OC=CC=1)C1OC=CC=1.CN1C(=O)CCC1.C([Sn](CCCC)(CCCC)CCCC)C=C>CCOC(C)=O>[CH2:29]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH:28]=[CH2:27]

参加物

6

反応物 4

HCID 13387N-methyl-2-pyrrolidoneHCID 90628AllyltributylstannaneHCID 521585Tris(furan-2-yl)phosphaneHCID 68580010HCID 68580010、化合物2 回

生成物 1

HCID 68579778HCID 68579778、化合物収率 774.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

Methyl 3-bromo-5-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}benzoate (Intermediate 104, 300 mg, 0.73 mmol), tris(dibenzylidineacetone)dipalladium (0) (26 mg, 0.03 mmol), trifurylphosphine (14 mg, 0.06 mmol) were weighed into a flask and placed under argon. NMP (3 ml) was added, followed by the dropwise addition of allyltributyl tin (0.25 ml, 0.80 mmol). The mixture was stirred at 100° C. After 64 h, the mixture was diluted with EtOAc and washed sequentially with water followed by brine. The organic phase was dried over MgSO4 and concentrated to dryness. The crude material was purified by chromatography on silica gel using 25% EtOAc/hexanes to give 174 mg of the title product.

後処理

  1. washwashed sequentially with water
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated to dryness
  4. customThe crude material was purified by chromatography on silica gel using 25% EtOAc/hexanes

出典と根拠

ORDレコード
ord-2d7099f7c9bf4f63bdc8f16684fcfa92
出典データセット
uspto-grants-2010_05
特許番号
US07709503B2

反応ノート

読み込み中…