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

HRID 1021021

反応式

HRID 1021021 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
140 °C

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-61fd4471621b4c6fb43a1aacaeb7692b
出典データセット
uspto-grants-2014_05
特許番号
US08716495B2

関連ノート

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