Morpholine → 4-((5-Oxo-2-pyrrolidinyl)carbonyl)morpholine

HRID 1021021

반응식

HRID 1021021 반응식
CO[C:3](=[O:10])[C@@H:4]1[CH2:8][CH2:7][C:6](=[O:9])[NH:5]1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C1(C)C(C)=CC=CC=1>[N:11]1([C:3]([CH:4]2[NH:5][C:6](=[O:9])[CH2:7][CH2:8]2)=[O:10])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

참가 물질

4

반응물 2

HCID 8083MorpholineHCID 78646Methyl 5-oxo-L-prolinate

생성물 1

HCID 1035684-((5-Oxo-2-pyrrolidinyl)carbonyl)morpholine

시약·촉매·용매 1

HCID 7237O-Xylene용매

반응 조건

온도
140 °C

실험 절차

A mixture of 143 g of pyroglutamic acid methyl ester (1 mol) and 139 g morpholine (1.60 mol) in 900 ml of xylene is heated to 140° C. for 20 h. The xylene is evaporated to a volume of 500 ml. From the suspension obtained, the precipitate is filtered off, washed with THF to yield the desired compound after drying in vacuo. From the filtrate the solvent is evaporated completely. This crude product [(R/S)-5-(morpholine-4-carbonyl)pyrrolidin-2-one] is filtered over 800 g silica gel with THF as the solvent and evaporated to dryness to yield a second crop of the desired compound. This compound is used directly in the next step. HPLC analysis shows the material to be in an enantiomeric ratio: 55.8:44.2 [(4-a, R1=H; R4=morpholine): (4-b, R1=H; R4=morpholine), respectively].

후처리

  1. customThe xylene is evaporated to a volume of 500 ml
  2. customFrom the suspension obtained
  3. filtrationthe precipitate is filtered off
  4. washwashed with THF

출처 및 근거

ORD 기록
ord-61fd4471621b4c6fb43a1aacaeb7692b
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716495B2

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