Benzyl Alcohol → benzyl 2-(4-chlorophenyl)-1-phenyl-6,7-dihydro-5H-pyrrolizine-3-carboxylate

HRID 586631

Reaction equation

HRID 586631 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.C(N(CC)CC)C.[O:29]=[C:30](Cl)[O:31][C:32](Cl)(Cl)Cl.C(O)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1>[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:30]([O:31][CH2:32][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:29])[CH2:11][CH2:12][CH2:13]3)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471Triethylamine2×HCID 10426DiphosgeneHCID 99716566-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

Product 1

HCID 22335615benzyl 2-(4-chlorophenyl)-1-phenyl-6,7-dihydro-5H-pyrrolizine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 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 triethylamine (0.7 ml, 0.51 g, 5 mmol). 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. Benzyl alcohol (abs., 0.52 ml, 0.54 g) and triethylamine (0.7 ml, 0.51 g, 5 mmol) are then added, and the mixture is stirred at RT for a further 48 h. The reaction mixture is partitioned between water (30 ml) and diethyl ether (60 ml), and the ether phase is washed with NaOH (5%, 20 ml). An oily residue is obtained from the THF/ether phase dried using Na2SO4 sicc. after the removal of the solvent in vacuo.

Workup

  1. additionis added dropwise to this solution at RT
  2. stirringthe mixture is stirred at RT for a further 48 h
  3. customThe reaction mixture is partitioned between water (30 ml) and diethyl ether (60 ml)
  4. washthe ether phase is washed with NaOH (5%, 20 ml)
  5. customAn oily residue is obtained from the THF/ether phase
  6. customdried
  7. customafter the removal of the solvent in vacuo

Sources & evidence

ORD record
ord-f6734393cd064fb697e8dce92277960e
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Linked notes

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