Methanol → HCID 22335623, compound

HRID 586617Notes

Reaction equation

HRID 586617 reaction equation
[F: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.CO>C(Cl)(Cl)Cl>[F: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][CH3:32])=[O:29])[CH2:11][CH2:12][CH2:13]3)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 10426DiphosgeneHCID 15390832HCID 15390832, compound

Product 1

HCID 22335623HCID 22335623, compoundYield 176.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 6-(4-fluorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine (prepared according to Laufer et al., 1.11 g, 4 mmol) in CHCl3 (20 ml) is cooled to 0° C. in an ice bath, treated with triethylamine (0.44 g, 4.4 mmol), and diphosgene (0.43 g, 2.2 mmol), dissolved in CHCl3 (5 ml) is added dropwise. After addition is complete, the mixture is stirred at RT for a further 4 h in the cold. After addition of MeOH (4 ml), it is additionally stirred at RT for 16 h. The reaction solution is washed with water, and then with Na2CO3 solution (10%) until acid-free and finally washed again with water. The separated CHCl3 phase is dried using Na2SO4 sicc. and concentrated. As a residue, 1.3 g (100%) of methyl 2-(4-fluorophenyl)-1-phenyl-6,7-dihydro-5H-pyrrolizine-3-carboxylate are obtained (GC. 93%). The substance is used in the next reaction step without further purification.

Workup

  1. additionis added dropwise
  2. additionAfter addition
  3. stirringis additionally stirred at RT for 16 h
  4. washThe reaction solution is washed with water
  5. washwith Na2CO3 solution (10%) until acid-free and finally washed again with water
  6. dry with materialThe separated CHCl3 phase is dried
  7. concentrationand concentrated

Sources & evidence

ORD record
ord-62ac247eb5bd4a578afa3e122f701132
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

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