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Morpholine → Indolizine-1,3-dicarboxylic acid 1-benzyl ester

HRID 1527196
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HRID 1527196 반응식
[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]([C:20]([O:22]CC=C)=[O:21])[N:14]2[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCOCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]([C:20]([OH:22])=[O:21])[N:14]2[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

5

반응물 2

HCID 8083MorpholineHCID 68283672Indolizine-1,3-dicarboxylic acid 3-allyl ester 1-benzyl ester

생성물 1

HCID 68283859Indolizine-1,3-dicarboxylic acid 1-benzyl ester

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of indolizine-1,3-dicarboxylic acid 3-allyl ester 1-benzyl ester (300 mg, 0.895 mmol) in THF (6 mL) were added Pd(PPh3)4 (34.5 mg, 0.09 mmol) and morpholine (260 mg, 8.95 mmol). The reaction mixture was stirred at RT under nitrogen atmosphere for 30 min. The reaction mixture was diluted in EtOAC, extracted twice with HCl 1N and the combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated to give the desired compound which was used without further purification in the next step TLC, Rf (CH2Cl2/MeOH 9:1)=0.4: MS (LC/MS): 294.0 [M−H]−; tR (HPLC conditions a): 3.62 min.

후처리

  1. additionThe reaction mixture was diluted in EtOAC
  2. extractionextracted twice with HCl 1N
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a5e7958ccfe34a918c19e0826f2f70da
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09085555B2

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