Sodium Hydroxide → HCID 22335609, compound

HRID 586643Notes

Reaction equation

HRID 586643 reaction equation
[CH3:1][C:2]1[N:3]2[C:7](=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:9]=1)[CH2:6][CH2:5][CH2:4]2.[F:16][C:17]([F:28])([C:24]([F:27])([F:26])[F:25])[C:18]([F:23])([F:22])[C:19](Cl)=[O:20].[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>ClC(Cl)C.C(Cl)Cl>[F:25][C:24]([F:26])([F:27])[C:17]([F:16])([F:28])[C:18]([F:22])([F:23])[C:19]([C:9]1[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:7]2[N:3]([C:2]=1[CH3:1])[CH2:4][CH2:5][CH2:6]2)=[O:20]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 67810Heptafluorobutyryl ChlorideHCID 22335626HCID 22335626, compound

Product 1

HCID 22335609HCID 22335609, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent2×

Procedure

5-Methyl-7-phenyl-2,3-dihydro-1H-pyrrolizine (Example 30 c, 1.0 g, 0.005 mol), dissolved in dichloroethane (20 ml) is treated with heptafluorobutyryl chloride (0.83 ml, 1.3 g, 0.0055 mol) at RT and finally tin tetrachloride (0.7 ml, 1,56 g, 0.006 mol) in dichloroethane (5 ml) is added dropwise. The mixture warms to 35° C. and is stirred at RT for 16 h. The GC-MS analysis shows a 60% reaction. The reaction mixture is rendered alkaline with NaOH (25%, 25 ml) in an ice bath and, after addition of CH2Cl2 (25 ml), the organic phase is separated in a separating funnel. The alkali phase is extracted a further two times with dichloromethane (2×20 ml). These CH2Cl2 extracts are combined, dried over Na2SO4 sicc. and evaporated to dryness in vacuo.

Workup

  1. customwarms to 35° C.
  2. customa 60% reaction
  3. customthe organic phase is separated in a separating funnel
  4. extractionThe alkali phase is extracted a further two times with dichloromethane (2×20 ml)
  5. dry with materialdried over Na2SO4 sicc
  6. customand evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-e06b5fe8211a4c30b66d0c0d0b84cdfd
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

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