Diisopropylethylamine → HCID 57743052、化合物

HRID 2043690ノート

反応式

HRID 2043690 の反応式
O[CH:2]1O[C:5](=[O:7])[CH2:4][CH:3]1[CH2:8][CH2:9][CH3:10].CCN(C(C)C)C(C)C.Cl.[O:21]1[CH:25]=[C:24]([CH2:26][NH2:27])[CH:23]=[N:22]1>ClCCCl.CC(O)=O>[O:21]1[CH:25]=[C:24]([CH2:26][N:27]2[CH2:2][CH:3]([CH2:8][CH2:9][CH3:10])[CH2:4][C:5]2=[O:7])[CH:23]=[N:22]1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 222742301-(1,2-Oxazol-4-yl)methanamine--hydrogen chloride (1/1)HCID 235310715-hydroxy-4-propyldihydrofuran-2(3H)-one

生成物 1

HCID 57743052HCID 57743052、化合物収率 32.3%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 111,2-Dichloroethane溶媒2 回

実験手順

A solution of 5-hydroxy-4-propyldihydrofuran-2(3H)-one x252 (0.44 g, 3.0 mmol) in dry DCE (8 ml), DIEA (0.364 g, 2.8 mmol), and several drops AcOH is added to a suspension of 1-isoxazol-4-ylmethanamine hydrochloride x251 (0.46 g, 3.0 mmol) in dry DCE, and NaHB(OAc)3 (0.976 g, 2.3 mmol) is added in 50 min. The reaction mixture is stirred at room temperature for 72 h and washed with 20% K2CO3 (2×25 ml). The aqueous layer is subjected to extraction with dichloromethane (3×30 ml). The combined organic layers are washed with brine (40 ml), dried over Na2SO4, and evaporated. The residue (0.55 g) is purified by chromatography on silicagel (chloroform/ethyl acetate 1/1) to afford 0.202 g of 1-(isoxazol-4-ylmethyl)-4-propylpyrrolidin-2-one 157 (yield 0.202 g, 32%).

後処理

  1. additionis added in 50 min
  2. washwashed with 20% K2CO3 (2×25 ml)
  3. extractionThe aqueous layer is subjected to extraction with dichloromethane (3×30 ml)
  4. washThe combined organic layers are washed with brine (40 ml)
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue (0.55 g) is purified by chromatography on silicagel (chloroform/ethyl acetate 1/1)

出典と根拠

ORDレコード
ord-28b079f3fb3b455ea905b78765a71d86
出典データセット
uspto-grants-2013_11
特許番号
US08586623B2

反応ノート

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