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

HRID 1080187

反応式

HRID 1080187 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒2 回

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bab6c35b24144a70a953b2dbbdcb5bf7
出典データセット
uspto-grants-1996_12
特許番号
US05580872

関連ノート

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