Stannous Chloride → HCID 57886759, compound

HRID 1190916Notes

Reaction equation

HRID 1190916 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.Cl[Sn]Cl>C1COCC1.Cl>[F:1][C:2]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 67246961HCID 67246961, compound

Product 1

HCID 57886759HCID 57886759, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(2-fluoro-5-nitro-benzyl)-pyrrolidine (420 mg, 1.87 mmol) in THF (20 mL) was added a solution of SnCl2 (1421 mg, 7.49 mmol) in THF (5 mL) and HCl 1M (2.1 mL). The reaction mixture was refluxed for 4 h and concentrated. Saturated solution of NaHCO3 was added until pH8. Aqueous layer was extracted with CH2Cl2 (5×50 mL). The organic layer was dried over MgSO4, filtered, evaporated. Expected compound was precipited with MeOH and purified by TLC (DCM/MeOH/NH4OH//9.5/0.5/0.35) and obtained as a yellow oil (229.5 mg, 63% yield). MALDI-TOF: m/z 195.2 [M+H]+. 1H NMR (300 MHz, CDCl3) δ6.76; (dd, J=9.5 Hz and 8.7 Hz, 1H), 6.69; (dd, J=6.1 Hz and 2.9 Hz, 1H), 6.46; (ddd, J=8.7 Hz, 4.1 Hz and 2.9 Hz, 1H), 3.57; (d, J=1.6 Hz, 2H), 3.3-3.5; (s large, 2H), 2.5-2.6; (m, 2H), 1.7-1.8; (m, 4H). 13C NMR (75 MHz, CDCl3) δ117.5; (CH, d, J=3.5 Hz), 115.7; (CH, d, J=23.6 Hz), 115.0; (CH, d, J=7.7 Hz), 54.1; (CH2), 52.8; (CH2), 23.6; (CH2).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. concentrationconcentrated
  3. additionSaturated solution of NaHCO3 was added until pH8
  4. extractionAqueous layer was extracted with CH2Cl2 (5×50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by TLC (DCM/MeOH/NH4OH//9.5/0.5/0.35)

Sources & evidence

ORD record
ord-6dd04d6a5c91403ca8dacbae84d49de7
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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