Benzylamine → HCID 53317861, compound

HRID 599897Notes

Reaction equation

HRID 599897 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:15]=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C:10]=2[CH2:9]1)=O)(C)(C)C.C(OC(N1CCC(=O)CC1)=O)(C)(C)C.C(N)C1C=CC=CC=1.[O-]S([O-])(=O)=O.[Mg+2].COC1C=CC(C=C[N+]([O-])=O)=CC=1>C1(C)C=CC=CC=1.O.[Sn](CCCC)(CCCC)(Cl)Cl>[CH2:25]([N:14]1[C:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]=2[C:16]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)=[CH:15]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

9

Reactant 5

HCID 7504BenzylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2298434-Methoxy-beta-nitrostyreneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 67269773HCID 67269773, compound

Product 1

HCID 53317861HCID 53317861, compound

Reagents, catalysts & solvents 3

HCID 12688Dibutyltin dichlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

1-Benzyl-3-(4-methoxy-phenyl)-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester. To a solution of 0.50 g of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester and 260 μL of benzylamine in toluene (5 mL) was added 0.48 g of MgSO4 and 16.7 mg of Bu2SnCl2. After 1 h, 0.45 g of 1-methoxy-4-(2-nitro-vinyl)-benzene was added and the mixture was stirred for 16 h at RT. The mixture was then diluted with water (80 mL) and extracted with EtOAc (3×15 mL) and the combined organic layers were concentrated in vacuo. Chromatography on SiO2 (1 to 20% EtOAc/hexanes) afforded 0.38 g of the desired compound. MS (ESI): exact mass calculated for C26H30N2O3, 418.23. found, m/z 419.2 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×15 mL)
  2. concentrationthe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-688c96eca18f471db56cb77e2f6b145a
Source dataset
uspto-grants-2011_03
Patent number
US07897771B2

Reaction notes

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