Methanol → HCID 22335658, compound

HRID 586636Notes

Reaction equation

HRID 586636 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(CC)CC)C.[O:29]=[C:30](Cl)[O:31][C:32](Cl)(Cl)Cl.CO>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][CH3:32])=[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 887MethanolHCID 8471Triethylamine2×HCID 10426DiphosgeneHCID 14855804HCID 14855804, compound

Product 1

HCID 22335658HCID 22335658, compoundYield 178.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7-(4-Chlorophenyl)-6-phenyl-2,3-dihydro-1H-pyrrolizine (Example 21 b, 4.0 g, 13.6 mmol), dissolved in THF (25 ml) is treated with triethylamine (2.0 ml, 1.5 g, 15 mmol). A solution of diphosgene (1.5 g, 7.5 mmol), dissolved in THF (15 ml), is added dropwise to this solution at RT, and it is stirred for 12 h. Methanol (abs., 8.0 ml, 6.3 g, 200 mmol) and triethylamine (2.0 ml, 1.5 g, 15 mmol) are then added, and the mixture is stirred at RT for a further 48 h. The reaction mixture is concentrated in vacuo, ammonium salts are taken up in water (10 ml), and the residue which remains is filtered off with suction and dried. 4.7 g (98.3%) of crude product are obtained.

Workup

  1. additionis added dropwise to this solution at RT
  2. stirringthe mixture is stirred at RT for a further 48 h
  3. concentrationThe reaction mixture is concentrated in vacuo, ammonium salts
  4. filtrationthe residue which remains is filtered off with suction
  5. customdried

Sources & evidence

ORD record
ord-b7b920e6335f4874a416a4d4fcf580ea
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

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