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

HRID 2060236노트

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HRID 2060236 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-70 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-4522435021274fd3a1cbd5ed93c1147b
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278343B2

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