Diethyl 2-quinolinylmethylphosphonate → Diethyl (5,6,7,8-tetrahydroquinolin-2-yl-methyl)phosphonate

HRID 718666Notes

Reaction equation

HRID 718666 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>FC(F)(F)C(O)=O.O=[Pt]=O>[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][P:12](=[O:19])([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18]

Participants

4

Reactant 1

HCID 11011347Diethyl 2-quinolinylmethylphosphonate

Product 1

HCID 117732512Diethyl (5,6,7,8-tetrahydroquinolin-2-yl-methyl)phosphonate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of compound 58a (6.0 g, 17 mmol) in trifluoroacetic acid (20 mL) was hydrogenated at about 2 to 3 atm over PtO2 (0.4 g, 1.8 mmol) at 30° C. for 20 h. The resulting mixture was filtered through a pad of diatomaceous earth and the filtrate was concentrated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:2 v/v)) to obtain compound 58b as a colorless oil. Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H27N5O3: 284.1 (M+H). Found: 284.2.

Workup

  1. filtrationThe resulting mixture was filtered through a pad of diatomaceous earth
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue obtained
  4. customwas purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:2 v/v))

Sources & evidence

ORD record
ord-8539dcf4ea9f41b7accaae55a420426d
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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