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

HRID 1080187

Reaction equation

HRID 1080187 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
70 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bab6c35b24144a70a953b2dbbdcb5bf7
Source dataset
uspto-grants-1996_12
Patent number
US05580872

Linked notes

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