1-(4-Nitrophenyl)pyrrolid-3-yl methanesulphonate → 1'-(4-Nitrophenyl)[1,3]bipyrrolidinyl

HRID 719676Notes

Reaction equation

HRID 719676 reaction equation
CS(O[CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O>N1CCCC1>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:9][CH2:10][CH:6]([N:8]3[CH2:9][CH2:10][CH2:6][CH2:7]3)[CH2:7]2)=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

3

Reactant 1

HCID 120678141-(4-Nitrophenyl)pyrrolid-3-yl methanesulphonate

Product 1

HCID 208292301'-(4-Nitrophenyl)[1,3]bipyrrolidinylYield 53%

Reagents, catalysts & solvents 1

HCID 31268PyrrolidineSolvent

Procedure

5 g (0.0174 mol) of 1-(4-nitrophenyl)pyrrolid-3-yl methanesulphonate (2) were heated at 85° C. for 2 hours in 30 ml of pyrrolidine (mol). This mixture was poured into ice-cold water until crystallization takes place. After filtration and drying, the yellow powder obtained was chromatographed, eluting with dichloromethane/methanol (98/2), and 2.6 g of derivative (5) were recovered (53% yield).

Workup

  1. additionThis mixture was poured into ice-cold water until crystallization
  2. filtrationAfter filtration
  3. customdrying
  4. customthe yellow powder obtained
  5. customwas chromatographed
  6. washeluting with dichloromethane/methanol (98/2), and 2.6 g of derivative (5)
  7. customwere recovered (53% yield)

Sources & evidence

ORD record
ord-d6a8e9bd19624a5fa76c00387332dbe9
Source dataset
uspto-grants-2006_11
Patent number
US07132534B2

Reaction notes

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