Methanol → methyl 2-(4-chlorophenyl)-1-phenyl-6,7-dihydro-5H-pyrrolizine-3-carboxylate

HRID 586629Notes

Reaction equation

HRID 586629 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:14]3[N:10]([CH2:11][CH2:12][CH2:13]3)[CH:9]=2)=[CH:4][CH:3]=1.[O:22]=[C:23](Cl)[O:24][C:25](Cl)(Cl)Cl.CO>C1COCC1.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:14]3[N:10]([C:9]=2[C:23]([O:24][CH3:25])=[O:22])[CH2:11][CH2:12][CH2:13]3)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 10426DiphosgeneHCID 99716566-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

Product 1

HCID 22335649methyl 2-(4-chlorophenyl)-1-phenyl-6,7-dihydro-5H-pyrrolizine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

6-(4-Chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine (Example 17 a, 1.5 g, 5.1 mmol), dissolved in THF (10 ml), is treated with 1 drop of triethylamine (about 50 mg). A solution of diphosgene (0.5 g, 2.5 mmol), dissolved in THF (5 ml), is added dropwise to this solution at RT and it is stirred for 8 h. Methanol (abs., 3 ml) is then added, and the mixture is stirred at RT for a further 12 h. The solvent is completely removed in vacuo (45° C.). The resinous residue is dissolved in CHCl3 (20 ml) and washed twice with water (20 ml). After the removal of the solvent in vacuo, a residue which is recrystallized from a little diisopropyl ether is obtained from the CHCl3 phase dried using Na2SO4 sicc.

Workup

  1. additionis added dropwise to this solution at RT
  2. stirringthe mixture is stirred at RT for a further 12 h
  3. customThe solvent is completely removed in vacuo (45° C.)
  4. dissolutionThe resinous residue is dissolved in CHCl3 (20 ml)
  5. washwashed twice with water (20 ml)
  6. customAfter the removal of the solvent in vacuo
  7. customa residue which is recrystallized from a little diisopropyl ether
  8. customis obtained from the CHCl3 phase
  9. customdried

Sources & evidence

ORD record
ord-08fa2e60355a475ab1b6d1dab99d906c
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

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