Hydrochloric Acid → 7,7-dimethyl-2,3,4,6,7,8-hexahydro-1H-pyrido[3,4-b]pyrrolizin-1-one

HRID 520310Notes

Reaction equation

HRID 520310 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:9][C:8]2[N:4]([C:5]3[CH2:16][CH2:15][NH:14][C:13](=[O:17])[C:6]=3[C:7]=2C(O)=O)[CH2:3]1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.N1C2C(=CC=CC=2)C=CC=1.Cl>O.CN1C(=O)CCC1>[CH3:1][C:2]1([CH3:18])[CH2:9][C:8]2[N:4]([C:5]3[CH2:16][CH2:15][NH:14][C:13](=[O:17])[C:6]=3[CH:7]=2)[CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13181,10-PhenanthrolineHCID 7047QuinolineHCID 1177774077,7-dimethyl-1-oxo-2,3,4,6,7,8-hexahydro-1H-pyrido[3,4-b]pyrrolizine-9-carboxylic acid

Product 1

HCID 1177774997,7-dimethyl-2,3,4,6,7,8-hexahydro-1H-pyrido[3,4-b]pyrrolizin-1-oneYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A microwave vial was charged with 137m (900 mg, 3.63 mmol), Cu2O (26 mg, 0.18 mmol), phenanthroline (66 mg, 0.36 mmol), quinoline (3 g, 23 mmol) and NMP (8 mL). The reaction mixture was microwaved at 200° C. for 3 h. See FIG. 2. Water was added and the mixture was neutralized to pH 7 by addition of 1N HCl and extracted with EA (50 mL×3). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH=10/1) to give 7,7-dimethyl-2,3,4,6,7,8-hexahydro-1H-pyrido[3,4-b]pyrrolizin-1-one 137n (450 mg, 61%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 6.18 (t, J=1.2 Hz, 1H), 5.16 (s, 1H), 3.57 (s, 4H), 2.76 (t, J=6.9 Hz, 2H), 2.64 (d, J=1.1 Hz, 2H), 1.25 (s, 6H); MS-ESI [M+H]+=205.1.

Workup

  1. customThe reaction mixture was microwaved at 200° C. for 3 h
  2. extractionextracted with EA (50 mL×3)
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (DCM/MeOH=10/1)

Sources & evidence

ORD record
ord-12644e08f3f7496295717a1e60334934
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

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