Azido(trimethyl)stannane → HCID 178499754, compound

HRID 1802774Notes

Reaction equation

HRID 1802774 reaction equation
[CH3:1][O:2][C:3](=[O:21])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]#[N:20])=[CH:8][CH:7]=1.[N:22]([Sn](C)(C)C)=[N+:23]=[N-:24]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3](=[O:21])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[NH:24][N:23]=[N:22][N:20]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 67158683HCID 67158683, compound

Product 1

HCID 178499754HCID 178499754, compoundYield 139.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of (E)-3-{4-[1-(2-cyano-ethyl)-pyrrolidin-2-yl]-phenyl}-acrylic acid methyl ester (1.0 g, 3.5 mmol) in xylene (35 mL) was added azidotrimethyltin (1.09 g, 5.30 mmol) and the reaction solution was stirred at 130° C. for 16 h. The solvent was removed under reduced pressure and the residue was dissolved in an aqueous sodium hydroxide solution, washed with ethyl acetate, and neutralized with 1 N hydrochloride. A yellow oil was separated from the aqueous layer which was extracted with methylene chloride:ethanol (4:1) several times. The organic layers were combined with the yellow oil, dried over sodium sulfate, filtrated and concentrated in vacuo to give 1.6 g of a yellow oil, which was used to the next step without further purification. LCMS (m/z): 328.0 (M+1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in an aqueous sodium hydroxide solution
  3. washwashed with ethyl acetate
  4. customA yellow oil was separated from the aqueous layer which
  5. extractionwas extracted with methylene chloride:ethanol (4:1) several times
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltrated
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fbf382bb7086403db74b373e77912b2a
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

Loading…