Ethyl chloroformate → 1-(4-Methoxy-benzoyl)-pyrrolidine-3,3-dicarboxylic acid diethyl ester

HRID 2060236ノート

反応式

HRID 2060236 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:11]([O:13][C:14]([CH:16]1[CH2:20][CH2:19][N:18]([C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH2:17]1)=[O:15])[CH3:12].Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33]>O1CCCC1>[CH2:11]([O:13][C:14]([C:16]1([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:20][CH2:19][N:18]([C:21](=[O:30])[C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[CH2:17]1)=[O:15])[CH3:12]

参加物

5

反応物 3

HCID 10928Ethyl chloroformateHCID 2733832Lithium HexamethyldisilazideHCID 593221751-(4-Methoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester

生成物 1

HCID 593222271-(4-Methoxy-benzoyl)-pyrrolidine-3,3-dicarboxylic acid diethyl ester収率 94%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

Lithium bis(trimethylsilyl)amide (1000 mL of a 1.0M solution in tetrahydrofuran, 1.0 mol) was added to a stirred solution of 1-(4-methoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester (±) (268 g, 0.97 mol) (see Preparation 2) in THF (1600 mL) at −70° C. The mixture was stirred for 20 mins at −70° C. then ethyl chloroformate (104 mL, 1.09 mol) was added over 15 minutes. The resulting mixture was stirred at −60° C. for 1 hour. The reaction mixture was quenched with 10% citric acid aqueous solution (1200 mL) at −50° C. then warmed to room temperature. The organic layer was separated, washed with saturated aqueous NaHCO3 (1200 mL) and water (1200 mL) then concentrated under reduced pressure to afford the title compound as an orange oil (316.0 g, 94%).

後処理

  1. stirringThe resulting mixture was stirred at −60° C. for 1 hour
  2. customThe reaction mixture was quenched with 10% citric acid aqueous solution (1200 mL) at −50° C.
  3. temperaturethen warmed to room temperature
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaHCO3 (1200 mL) and water (1200 mL)
  6. concentrationthen concentrated under reduced pressure

出典と根拠

ORDレコード
ord-4522435021274fd3a1cbd5ed93c1147b
出典データセット
uspto-grants-2012_10
特許番号
US08278343B2

反応ノート

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