tert-butyl N-(pyrrolidin-3-yl)carbamate → 8-(3-Amino-1-pyrrolidinyl)-4H-quinolizin-4-one-3-carboxylic acid hydrochloride

HRID 1080187

반응식

HRID 1080187 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]([O:14]CC)=[O:13])[C:6]2=[O:17].C(OC([NH:25][CH:26]1[CH2:30][CH2:29][NH:28][CH2:27]1)=O)(C)(C)C>N1C=CC=CC=1>[ClH:1].[NH2:25][CH:26]1[CH2:30][CH2:29][N:28]([C:2]2[CH:3]=[CH:4][N:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[C:7]([C:12]([OH:14])=[O:13])[C:6]3=[O:17])[CH2:27]1

참가 물질

4

반응물 2

HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 3314858Ethyl 8-chloro-4-oxo-4H-quinolizine-3-carboxylate

생성물 1

HCID 882526988-(3-Amino-1-pyrrolidinyl)-4H-quinolizin-4-one-3-carboxylic acid hydrochloride수율 72.3%

시약·촉매·용매 1

HCID 1049Pyridine용매2회

반응 조건

온도
70 °C

실험 절차

Ethyl 8-chloro-4H-quinolizin-4-one-3-carboxylate (1.0 g, 3.97 mmol), from Step 3, was dissolved in 20 mL of dry pyridine under a nitrogen atmosphere. To the resultant solution was added a solution of 1.85 g (9.92 mmol) of 3-(N-t-butoxycarbonylamino)pyrrolidine in 5 mL of dry pyridine and the reaction mixture was heated at 70° C. for 4.5 hours. The reaction mixture was then concentrated in vacuo in order to remove all of the pyridine. The dry residue (3.124 g) was purified by chromatography on silica gel eluted with 2% methanol in methylene chloride to afford 0.889 g (56% yield) of the title compound.

후처리

  1. concentrationThe reaction mixture was then concentrated in vacuo in order
  2. customto remove all of the pyridine
  3. customThe dry residue (3.124 g) was purified by chromatography on silica gel
  4. washeluted with 2% methanol in methylene chloride

출처 및 근거

ORD 기록
ord-bab6c35b24144a70a953b2dbbdcb5bf7
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05580872

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