Dimethyl malonate → HCID 68734273、化合物

HRID 387538ノート

反応式

HRID 387538 の反応式
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].CCN(C(C)C)C(C)C.CO[CH:21]1[N:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:24]([CH3:34])([CH3:33])[CH2:23][CH2:22]1.[NH4+].[Cl-]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:29]([O:28][C:26]([N:25]1[C:24]([CH3:34])([CH3:33])[CH2:23][CH2:22][CH:21]1[CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[O:27])([CH3:32])([CH3:30])[CH3:31]

参加物

7

反応物 4

HCID 7943Dimethyl malonateHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 59564912HCID 59564912、化合物

生成物 1

HCID 68734273HCID 68734273、化合物収率 75.9%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒4 回

実験手順

TiCl4 (1.9 mL, 1.9 mmol) as a 1M DCM solution was added to a solution of dimethyl malonate (0.195 mL, 1.70 mmol) in DCM (10 mL) at 0° C. under N2, and the reaction was stirred for 10 minutes. DIEA (0.3 mL, 1.7 mmol) was then added slowly, and the reaction was stirred for an additional 30 minutes at 0° C. A DCM (2 mL) solution of tert-butyl 5-methoxy-2,2-dimethylpyrrolidine-1-carboxylate (325 mg, 1.4 mmol) was then slowly added dropwise, and the reaction was stirred at 0° C. for 10 minutes. Saturated NH4Cl was then added, and then reaction was diluted with DCM and washed with saturated NaHCO3. The organic fractions were then dried, filtered, and concentrated to give the crude product, which was purified by column chromatography (500:50-500:90 hexanes:EtOAc) to give dimethyl 2-(1-(tert-butoxycarbonyl)-5,5-dimethylpyrrolidin-2-yl)malonate (0.35 g, 75%).

後処理

  1. stirringthe reaction was stirred for an additional 30 minutes at 0° C
  2. stirringthe reaction was stirred at 0° C. for 10 minutes
  3. customreaction
  4. washwashed with saturated NaHCO3
  5. customThe organic fractions were then dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product, which
  9. customwas purified by column chromatography (500:50-500:90 hexanes:EtOAc)

出典と根拠

ORDレコード
ord-d9be5ff4f15f4702be1c50661b5df228
出典データセット
uspto-grants-2013_02
特許番号
US08372842B2

反応ノート

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