1-[2-[4-[3-[4-[3-(1-Pyrrolidinyl)-1-propynyl]benzyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine Dioxalate → (E)-1-[2-[4-[3-[4-[3-(1-Pyrrolidinyl)-1-propenyl]benzyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine Dioxalate

HRID 1070330Notes

Reaction equation

HRID 1070330 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[C:7]([OH:12])(=[O:11])[C:8]([OH:10])=[O:9].[N:13]1([CH2:18][C:19]#[C:20][C:21]2[CH:50]=[CH:49][C:24]([CH2:25][C:26]3[C:27]4[CH:48]=[CH:47][CH:46]=[CH:45][C:28]=4[S:29][C:30]=3[C:31]3[CH:44]=[CH:43][C:34]([O:35][CH2:36][CH2:37][N:38]4[CH2:42][CH2:41][CH2:40][CH2:39]4)=[CH:33][CH:32]=3)=[CH:23][CH:22]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1>N1C=CC=CC=1.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[C:7]([OH:12])(=[O:11])[C:8]([OH:10])=[O:9].[N:13]1([CH2:18]/[CH:19]=[CH:20]/[C:21]2[CH:22]=[CH:23][C:24]([CH2:25][C:26]3[C:27]4[CH:48]=[CH:47][CH:46]=[CH:45][C:28]=4[S:29][C:30]=3[C:31]3[CH:44]=[CH:43][C:34]([O:35][CH2:36][CH2:37][N:38]4[CH2:39][CH2:40][CH2:41][CH2:42]4)=[CH:33][CH:32]=3)=[CH:49][CH:50]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 867570901-[2-[4-[3-[4-[3-(1-Pyrrolidinyl)-1-propynyl]benzyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine Dioxalate

Product 1

HCID 86757091(E)-1-[2-[4-[3-[4-[3-(1-Pyrrolidinyl)-1-propenyl]benzyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine DioxalateYield 61.5%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 1049PyridineSolvent2×

Procedure

A solution of 1-[2-[4-[3-[4-[3-(1-pyrrolidinyl)-1-propynyl]benzyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine (Example 129, Part D; 300 mg, 0.576 mmol) in 40 mL of pyridine was treated with a slurry of Lindlar catalyst (Pd/CaCO3, Pb poisoned; 100 mg) in 10 mL of pyridine. The resulting mixture was stirred under an atmospheric pressure of H2 at room temperature for 3 h. The reaction mixture was filtered through a pad of diatomaceous earth and concentrated in vacuo. Purification by radial chromatography (SiO2; 5% MeOH in CHCl3, saturated with NH4OH) gave 185 mg (0.354 mmol, 61%) of a yellow oil which was converted to the dioxalate salt according to the procedure described in Example 1, Part C.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. concentrationconcentrated in vacuo
  3. customPurification by radial chromatography (SiO2; 5% MeOH in CHCl3, saturated with NH4OH)

Sources & evidence

ORD record
ord-2c9db193c6b24fdf87ae81db900ed380
Source dataset
uspto-grants-2001_06
Patent number
US06251921B1

Reaction notes

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