Pyrrolidine → HCID 62177350, compound

HRID 1916620Notes

Reaction equation

HRID 1916620 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][NH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.C(O)(=O)C>[CH3:6][NH:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17]

Participants

7

Reactant 4

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 38542614-(methylamino)-3-nitrobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 62177350HCID 62177350, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

5.55 g (78.0 mmol) pyrrolidine are added to a solution of 4.70 g (26.1 mmol) 4-methylamino-3-nitro-benzaldehyde in 100 mL THF and the reaction mixture is acidified with glacial acetic acid. 6.36 g (30.0 mmol) NaBH(OAc)3 are added and the reaction mixture is stirred overnight at RT. The mixture is combined with saturated NaHCO3 solution and the aqueous phase is extracted twice with EtOAc. The combined organic extracts are washed with 200 mL semisaturated NaHCO3 solution and dried over MgSO4. The solvent is eliminated i.vac. and further purification is carried out by column chromatography on silica gel (gradient: DCM to DCM/MeOH 9:1).

Workup

  1. extractionthe aqueous phase is extracted twice with EtOAc
  2. washThe combined organic extracts are washed with 200 mL
  3. dry with materialdried over MgSO4
  4. customand further purification

Sources & evidence

ORD record
ord-33ef7ad9873d47acb3ee82c9b720e312
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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