Hydrochloric Acid → HCID 57980031, compound

HRID 1677154Notes

Reaction equation

HRID 1677154 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([N:18]3[CH2:22][CH2:21][CH2:20][C@H:19]3[CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.O.O.Cl[Sn]Cl.Cl>CCO>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]([N:18]3[CH2:22][CH2:21][CH2:20][C@H:19]3[CH2:23][N:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)=[O:17])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 57980075HCID 57980075, compound

Product 1

HCID 57980031HCID 57980031, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Procedure OO: 160 mg of (4′-Nitro-biphenyl-4-yl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone (0.43 mmol) is put into the solution of 485 mg of SnCl2.2H2O (2.15 mmol) in 1.0 ml of EtOH. 1.0 ml of conc. HCl is added to the mixture and heated at 60° C. for 30 min. EtOH is removed in vacuo and the solution is made it to pH=12.0 by aqueous NaOH. This mixture is extracted with dichloromethane, dried over Na2SO4 and evaporated. The crude product is applied to SCX column and washed by MeOH and the desired product is eluted with 2M NH3 in MeOH. The elution is concentrated and applied to silica-gel column chromatography (CH2Cl2:2M NH3 in MeOH=20:1) to give the title compound. 77 mg (51%) Observed mass; 350 (M+1)

Workup

  1. customEtOH is removed in vacuo
  2. extractionThis mixture is extracted with dichloromethane
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. washwashed by MeOH
  6. washthe desired product is eluted with 2M NH3 in MeOH
  7. washThe elution
  8. concentrationis concentrated

Sources & evidence

ORD record
ord-cb8e1b9f091f45488b614fcbcce61f0d
Source dataset
uspto-grants-2011_08
Patent number
US08008301B2

Reaction notes

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