Pyrrolidine → 1'-Benzyl-[1,3']bipyrrolidinyl

HRID 1916594Notes

Reaction equation

HRID 1916594 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[CH2:20]([N:27]1[CH2:31][CH2:30][CH2:29][C:28]1=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])(O)=O.[Na+]>C1COCC1.C(O)(=O)C>[CH2:20]([N:27]1[CH2:31][CH2:30][CH:29]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 31268PyrrolidineHCID 791761-Benzyl-3-pyrrolidoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 231459231'-Benzyl-[1,3']bipyrrolidinyl

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.82 g (18.0 mmol) NaBH(OAc)3 are added to a solution of 1.23 mL (15.0 mmol) pyrrolidine and 2.41 mL (15.0 mmol) N-benzylpyrrolidinone in 100 mL THF and acidified with 2 mL acetic acid. The reaction is stirred overnight at RT. The reaction solution is combined with 200 mL saturated NaHCO3 solution and extracted twice with 200 mL EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out by column chromatography on silica gel (EtOAc/MeOH/NH3 8:2:0.2).

Workup

  1. extractionextracted twice with 200 mL EtOAc
  2. dry with materialThe organic phase is dried over MgSO4
  3. customThe purification

Sources & evidence

ORD record
ord-49cc2a5a4cad42bbae42188f09ae7fad
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

Loading…