Ethanol → HCID 22335612, compound

HRID 586635Notes

Reaction equation

HRID 586635 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][N:11]3[C:15]=2[CH2:14][CH2:13][CH2:12]3)=[CH:4][CH:3]=1.C(N([CH2:27][CH3:28])CC)C.[O:29]=[C:30](Cl)[O:31]C(Cl)(Cl)Cl.C(O)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:10]([C:30]([O:31][CH2:27][CH3:28])=[O:29])[N:11]3[C:15]=2[CH2:14][CH2:13][CH2:12]3)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471Triethylamine2×HCID 10426DiphosgeneHCID 14855804HCID 14855804, compound

Product 1

HCID 22335612HCID 22335612, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7-(4-Chlorophenyl)-6-phenyl-2,3-dihydro-1H-pyrrolizine (Example 21 b, 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, it is stirred for 12 h, ethanol (abs., 3 ml, 2.37 g, 51 mmol) and triethylamine (0.7 ml, 0.51 g, 5 mmol) are added, and the mixture is stirred at RT for a further 72 h. The reaction mixture is concentrated in vacuo, and the residue is crystallized from EtOH and dried.

Workup

  1. additionis added dropwise to this solution at RT
  2. stirringthe mixture is stirred at RT for a further 72 h
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. customthe residue is crystallized from EtOH
  5. customdried

Sources & evidence

ORD record
ord-c23af2ca415c46b68c93a3ca413156d6
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

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