Dibutyltin oxide → 5-[4-(3-Fluoro-phenyl)-3-hydroxy-butyl]-1-[6-(2H-tetrazol-5-yl)-hexyl]-pyrrolidin-2-one

HRID 1582666Notes

Reaction equation

HRID 1582666 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([OH:26])[CH2:10][CH2:11][CH:12]2[CH2:16][CH2:15][C:14](=[O:17])[N:13]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[N:25])[CH:5]=[CH:6][CH:7]=1.[N:27]([Si](C)(C)C)=[N+:28]=[N-:29].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([OH:26])[CH2:10][CH2:11][CH:12]2[N:13]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]3[N:27]=[N:28][NH:29][N:25]=3)[C:14](=[O:17])[CH2:15][CH2:16]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 227187697-{2-[4-(3-Fluoro-phenyl)-3-hydroxy-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile

Product 1

HCID 101508285-[4-(3-Fluoro-phenyl)-3-hydroxy-butyl]-1-[6-(2H-tetrazol-5-yl)-hexyl]-pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Following the procedure described for Example 6, Step C, 7-{2-[4-(3-fluoro-phenyl)-3-hydroxy-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile (141.3 mg, 0.392 mmol) was reacted with azidotrimethylsilane (0.210 mL, 1.57 mmol) and dibutyltin oxide (29 mg, 0.116 mmol) in toluene (8 mL) heated under reflux for 72 h. Purification by medium pressure chromatography (CH2Cl2 to 2% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2 to 6% MeOH in CH2Cl2) provided the title compound of Example 5C. (101.5 mg). 1H NMR (CDCl3) δ7.26 (m, 1H), 6.94 (m, 3H), 3.87 (m, 1H), 3.70 (m, 1H), 3.52 (m, 1H), 2.98 (m, 3H), 2.78 (m, 2H), 2.48 (m, 2H), 2.20 (m, 1H), 1.89-1.24 (m, 1 4H); MS 404.2 (M+1), 401.9 (M−1).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 72 h
  3. customPurification by medium pressure chromatography (CH2Cl2 to 2% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2 to 6% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-4a007cd58bb04d22a9aef46f22f42fd3
Source dataset
uspto-grants-2004_05
Patent number
US06737437B2

Reaction notes

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